WO2023099297A1 - Synthesis of hmo butyrate - Google Patents

Synthesis of hmo butyrate Download PDF

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Publication number
WO2023099297A1
WO2023099297A1 PCT/EP2022/082914 EP2022082914W WO2023099297A1 WO 2023099297 A1 WO2023099297 A1 WO 2023099297A1 EP 2022082914 W EP2022082914 W EP 2022082914W WO 2023099297 A1 WO2023099297 A1 WO 2023099297A1
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formula
compound
substituents
process according
present
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PCT/EP2022/082914
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French (fr)
Inventor
Werner Bonrath
Casper DE-BOER
Ronald Gebhard
Alissa GOETZINGER
Bettina Wuestenberg
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Dsm Ip Assets B.V.
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Publication of WO2023099297A1 publication Critical patent/WO2023099297A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms

Definitions

  • the present invention relates to specific butyrate compounds and to a new and improved synthesis of specific butyrates as well their use.
  • Butyrate compounds are very useful compounds, either as such or as intermediates in organic synthesis.
  • butyrates fuel colonocytes help provide an oxygen-free environment in which beneficial gut microbes thrive. This keeps inflammation in check, gut cells healthy and gut bacteria in a good state.
  • Butyrates stop some of the pro-inflammatory substances in the human body from working.
  • the anti-inflammatory effect of butyrate reduces oxidative stress and controls the damage caused by free radicals.
  • GLP-1 glucagon-like peptide-1
  • PYY peptide YY
  • the goal of the present invention was to provide a way to produce butyrate compounds having all advantages but not having the strong unpleasant odour in a good yield.
  • the present invention relates to a process (P) for producing a compound of formula (I) wherein R, Ri , R2, R3, R4 Rs, Re R7, Rs and R9 are either with the proviso that less than 5 substituents are H, characterised in that a compound of formula (II) is reacted with a compound of formula (III) wherein X is a halogen atom, -OH or the following moiety
  • the process according to the present invention relates to a process for producing a compound of formula (I) wherein
  • R, Ri , R2, R3, 4 Rs, Re R7, Rs and R9 are either with the proviso that less than 4 substituents are H. (more preferably less than 3 substituents are H, even more preferably less than 2 substituents are H, more preferably none of the substituents are H).
  • the present invention relates to a process (P1 ), which is process (P), wherein the compound of formula (I) less than 4 substituents are H.
  • the present invention relates to a process (PT), which is process (P), wherein the compound of formula (I) less than 3 substituents are H.
  • the present invention relates to a process (P1”), which is process (P), wherein the compound of formula (I) less than 2 substituents are H. Therefore, the present invention relates to a process (PT”), which is process (P), wherein the compound of formula (I) none of the substituents are H.
  • This compound is known as 2'-Fucosyllactose (2’-FL).
  • HMO human milk oligosaccharide
  • HMOs Human milk oligosaccharides
  • 2’-FL has a positive influence on short-chain fatty acids in the gut as it promotes the n-butyrate production.
  • 2’-FL can be isolated or synthesized. Alternatively, it is also available commercially from a variety of suppliers.
  • the present invention relates to a process (P2), which is the process (P), (P1 ), (PT), (P1”) or (PT”), wherein the 2’-FL is reacted with a compound of formula (HI)
  • the present invention relates to a process (P2’), which is the process (P), (P1 ), (PT), (P1”) or (PT”), wherein the 2’-FL is reacted with a compound of formula (HI) O wherein X is a -Cl, -OH or the following moiety (* marks the bond to the CO group).
  • the present invention relates to a process (P2”), which is the process (P), (P1 ), (PT), (P1 ”) or (PT”), wherein the 2’-FL is reacted with a compound of formula (Hla)
  • the process according to the present invention is carried out in the presence of at least one polar, basic, inert solvent.
  • Such a solvent is usually chosen from the group consisting of pyridines, such as pyridine, substituted pyridines such as dimethyl aminopyridines, or methyl pyridines, or trialkylamines such as triethylamine, diisopropylethylamine, or tributylamine.
  • the present invention relates to a process (P3), which is the process (P), (P1 ), (PT), (P1 ”), (PT”), (P2), (P2’) or (P2”), wherein the reaction is carried out in the presence of at least one polar, basic, inert solvent.
  • the present invention relates to a process (P3’), which is the process (P3), wherein the at least one polar, basic, inert solvent is chosen from the group consisting of pyridines, substituted pyridines and trialkylamines.
  • the present invention relates to a process (P3”), which is the process (P3), wherein the at least one polar, basic, inert solvent is chosen from the group consisting of pyridines, dimethyl aminopyridines, methyl pyridines, triethylamine, diisopropylethylamine and tributylamine.
  • the solvent is used in molar excess in view of the compound of formula (II).
  • the amount of the solvent is not critical for the process according to the present invention. Therefore, the present invention relates to a process (P4), which is the process (P), wherein the solvent is used in molar excess in view of the compound of formula (II).
  • the compound of formula (III) needs to be added in such an amount that all (or at least 6 positions) of the compound of formula (II) are butyrated.
  • compound of formula (III) is used in a molar ratio in regard to compound of formula (II) of 6:1 to 100 (preferably 10:1 to 100:1 ).
  • the present invention relates to a process (P5), which is the process (P), (P1 ), (PT), (P1 ”), (PT”), (P2), (P2’), (P2”), (P3), (P3’), (P3”) or (P4), wherein the compound of formula (III) is used in a molar ratio in regard to compound of formula (II) of 6:1 to 100.
  • the present invention relates to a process (P5’), which is the process (P), (P1 ), (PT), (P1”), (PT”), (P2), (P2’), (P2”), (P3), (P3’), (P3”) or (P4), wherein the compound of formula (III) is used in a molar ratio in regard to compound of formula (II) of 10:1 to 100:1.
  • process of the present invention can be carried out in a mixture of organic and inorganic bases.
  • Organic bases are i.e., pyridines, such as pyridine; substituted pyridines such as dimethyl aminopyridines, or methyl pyridines; or trialkylamines such as triethylamine, diisopropylethylamine, or tributylamine.
  • Inorganic bases are i.e., carbonates, such as potassium or sodium carbonate and the corresponding hydrogen carbonates.
  • the present invention relates to a process (P6), which is process (P), (P1 ), (PT), (P1 ”), (PT”), (P2), (P2’), (P2”), (P3), (P3’), (P3”), (P4), (P5) or (P5’), wherein the reaction is carried in a mixture of at least one organic base and at least one inorganic base. Therefore, the present invention relates to a process (P6’), which is process (P6), wherein the at least one organic base is chosen from the group consisting of pyridines, substituted pyridines and trialkylamines.
  • the present invention relates to a process (P6”), which is process (P6), wherein the at least one organic base is chosen from the group consisting of pyridine, dimethyl aminopyridines, methyl pyridines, triethylamine, diisopropylethylamine and tributylamine.
  • the present invention relates to a process (P6’”), which is process (P6), wherein the at least one inorganic base is chosen from the group consisting of carbonates and the corresponding hydrogen carbonates.
  • the present invention relates to a process (P6””), which is process (P6), wherein the at least one inorganic base is chosen from potassium carbonate, sodium carbonate and the corresponding hydrogen carbonates.
  • the reaction is carried out at a temperature of between 15-50° C (more preferably at a temperature of between 20-30° C).
  • the present invention relates to a process (P7), which is process (P), (P1 ), (PT), (P1 ”), (PT”), (P2), (P2’), (P2”), (P3), (P3’), (P3”), (P4), (P5), (P5’), (P6), (P6’), (P6”), (P6’”) or (P6””), wherein the reaction is carried out at a temperature of 15 - 50° C.
  • the present invention relates to a process (P7’), which is process (P), (P1 ), (PT), (P1”), (PT”), (P2), (P2’), (P2”), (P3), (P3’), (P3”), (P4), (P5), (P5’), (P6), (P6’), (P6”), (P6’”) or (P6””), wherein the reaction is carried out at a temperature of 20-30° C.
  • reaction compound compound of formula (I)
  • reaction product of step (i) can be purified. This is also done by commonly known and used methods.
  • compounds of formula (I) are new.
  • the present invention relates to compounds of formula (I) wherein R, Ri , R2, R3, R4 Rs, Re R7, Rs and R9 are either with the proviso that less than 4 substituents are H. (more preferably less than 3 substituents are H, even more less than 2 substituents are H, more preferably wherein none of the substituents are H).
  • R, Ri , R2, R3, R4 Rs, Re R7, Rs and R9 are either with the proviso that less than 4 substituents are H. (more preferably less than 3 substituents are H, even more less than 2 substituents are H, more preferably wherein none of the substituents are H).
  • the following Examples illustrate the invention further without limiting it. All percentages and parts, which are given, are related to the weight and the temperatures are given in °C, and the pressures are absolute pressures when not otherwise stated.
  • the reaction mixture was concentrated under reduced pressure.
  • the residue was diluted with dichloromethane and extracted several times with a total 125 of sat. aq. mL NaHCChand once with brine, dried with magnesium sulfate, filtered, and concentrated under reduced pressure.
  • To the residue were added 50 mL of sat. aq. NaHCCh and the mixture was stirred overnight to hydrolyze excess butyric acid. It was then extracted several times with dichloromethane. The combined organic layers were washed with brine, dried with magnesium sulfate, filtered, and concentrated to give 0.46 g of a colorless gum.
  • the crude product was purified by chromatography (SiC>2, 40-60 micrometer, heptane/ethyl acetate, detected with ELSD).
  • the product was characterized by 1 H- and 13 C-NMR spectroscopy, IR-spectroscopy, and MS (high resolution).

Abstract

The present invention relates to new specific butyrate compounds to a new and improved synthesis of specific butyrates as well their use. Butyrate compounds are very useful compounds.

Description

Synthesis of HMO Butyrate
The present invention relates to specific butyrate compounds and to a new and improved synthesis of specific butyrates as well their use. Butyrate compounds are very useful compounds, either as such or as intermediates in organic synthesis.
It is known that butyrates fuel colonocytes, and in return these cells help provide an oxygen-free environment in which beneficial gut microbes thrive. This keeps inflammation in check, gut cells healthy and gut bacteria in a good state.
Higher butyrate levels have been shown to increase levels of glutathione, an antioxidant produced in the body’s cells which neutralises free radicals in the gut. This is good because free radicals are linked to inflammation and many diseases.
Butyrates stop some of the pro-inflammatory substances in the human body from working. The anti-inflammatory effect of butyrate reduces oxidative stress and controls the damage caused by free radicals.
Furthermore, research shows that butyrates enhance the secretion of gut hormones like glucagon-like peptide-1 (GLP-1 ) and peptide YY (PYY). GLP-1 increases insulin production and reduces glucagon production in the pancreas. PYY increases the uptake of glucose in both muscles and fatty tissue.
Increased production of short-chain fatty acids, including butyrate in the colon, increases the release of these gut hormones, indicating potential benefits for managing blood sugar levels and preventing weight gain.
The main problem with the butyrates is their strong (fishy) odour. Such an odour is such that most persons are not able to swallow such a compound even in very low concentration.
Due to the importance of butyrates, the goal of the present invention was to provide a way to produce butyrate compounds having all advantages but not having the strong unpleasant odour in a good yield.
Surprisingly, it was found that specific butyrate compounds as defined by the formula below can be obtained in good yields and selectivities by a new and easy process. Therefore, the present invention relates to a process (P) for producing a compound of formula (I)
Figure imgf000003_0001
wherein R, Ri , R2, R3, R4 Rs, Re R7, Rs and R9 are either
Figure imgf000003_0002
with the proviso that less than 5 substituents are H, characterised in that a compound of formula (II)
Figure imgf000003_0004
is reacted with a compound of formula (III)
Figure imgf000003_0003
wherein X is a halogen atom, -OH or the following moiety
O
Figure imgf000004_0001
(* marks the bond to the CO group).
Preferably, the process according to the present invention relates to a process for producing a compound of formula (I)
Figure imgf000004_0002
wherein
R, Ri , R2, R3, 4 Rs, Re R7, Rs and R9 are either
Figure imgf000004_0003
with the proviso that less than 4 substituents are H. (more preferably less than 3 substituents are H, even more preferably less than 2 substituents are H, more preferably none of the substituents are H).
Therefore, the present invention relates to a process (P1 ), which is process (P), wherein the compound of formula (I) less than 4 substituents are H.
Therefore, the present invention relates to a process (PT), which is process (P), wherein the compound of formula (I) less than 3 substituents are H.
Therefore, the present invention relates to a process (P1”), which is process (P), wherein the compound of formula (I) less than 2 substituents are H. Therefore, the present invention relates to a process (PT”), which is process (P), wherein the compound of formula (I) none of the substituents are H.
It is clear that it is possible to get mixtures of compounds of formula (I), which have a different substitution pattern.
In the following the process according to the present invention is discussed and described in more detail.
As stated above the starting material is the compound of formula (II)
Figure imgf000005_0001
This compound is known as 2'-Fucosyllactose (2’-FL).
2’-FL is a human milk oligosaccharide (HMO).
Human milk oligosaccharides (HMOs) are a family of structurally diverse unconjugated glycans that are highly abundant in and unique to human milk. Originally, HMOs were proposed to be prebiotic "bifidus factors," or human milk glycans found to promote growth in Bifidobactenal species of the gut and found uniquely in the stool of breastfed infants compared to formula fed infants.
Furthermore, 2’-FL has a positive influence on short-chain fatty acids in the gut as it promotes the n-butyrate production.
2’-FL can be isolated or synthesized. Alternatively, it is also available commercially from a variety of suppliers.
2’-FL is reacted with a compound of formula (III)
Figure imgf000006_0001
wherein X is a halogen atom, -OH or the following moiety
Figure imgf000006_0002
(* marks the bond to the CO group).
Preferably
Figure imgf000006_0003
More preferably the compound of formula (Illa)
Figure imgf000006_0004
is used.
Therefore, the present invention relates to a process (P2), which is the process (P), (P1 ), (PT), (P1”) or (PT”), wherein the 2’-FL is reacted with a compound of formula (HI)
O
/\ X ("D wherein X is a halogen atom, -OH or the following moiety O
Figure imgf000006_0005
(* marks the bond to the CO group).
Therefore, the present invention relates to a process (P2’), which is the process (P), (P1 ), (PT), (P1”) or (PT”), wherein the 2’-FL is reacted with a compound of formula (HI)
Figure imgf000006_0006
O wherein X is a -Cl, -OH or the following moiety
Figure imgf000007_0001
(* marks the bond to the CO group).
Therefore, the present invention relates to a process (P2”), which is the process (P), (P1 ), (PT), (P1 ”) or (PT”), wherein the 2’-FL is reacted with a compound of formula (Hla)
Figure imgf000007_0002
Usually and preferably, the process according to the present invention is carried out in the presence of at least one polar, basic, inert solvent.
Such a solvent is usually chosen from the group consisting of pyridines, such as pyridine, substituted pyridines such as dimethyl aminopyridines, or methyl pyridines, or trialkylamines such as triethylamine, diisopropylethylamine, or tributylamine.
Therefore, the present invention relates to a process (P3), which is the process (P), (P1 ), (PT), (P1 ”), (PT”), (P2), (P2’) or (P2”), wherein the reaction is carried out in the presence of at least one polar, basic, inert solvent.
Therefore, the present invention relates to a process (P3’), which is the process (P3), wherein the at least one polar, basic, inert solvent is chosen from the group consisting of pyridines, substituted pyridines and trialkylamines.
Therefore, the present invention relates to a process (P3”), which is the process (P3), wherein the at least one polar, basic, inert solvent is chosen from the group consisting of pyridines, dimethyl aminopyridines, methyl pyridines, triethylamine, diisopropylethylamine and tributylamine.
The solvent is used in molar excess in view of the compound of formula (II). The amount of the solvent is not critical for the process according to the present invention. Therefore, the present invention relates to a process (P4), which is the process (P),
Figure imgf000008_0001
wherein the solvent is used in molar excess in view of the compound of formula (II).
The compound of formula (III) needs to be added in such an amount that all (or at least 6 positions) of the compound of formula (II) are butyrated.
Usually the compound of formula (III) is used in a molar ratio in regard to compound of formula (II) of 6:1 to 100 (preferably 10:1 to 100:1 ).
Therefore, the present invention relates to a process (P5), which is the process (P), (P1 ), (PT), (P1 ”), (PT”), (P2), (P2’), (P2”), (P3), (P3’), (P3”) or (P4), wherein the compound of formula (III) is used in a molar ratio in regard to compound of formula (II) of 6:1 to 100.
Therefore, the present invention relates to a process (P5’), which is the process (P), (P1 ), (PT), (P1”), (PT”), (P2), (P2’), (P2”), (P3), (P3’), (P3”) or (P4), wherein the compound of formula (III) is used in a molar ratio in regard to compound of formula (II) of 10:1 to 100:1.
Furthermore, the process of the present invention can be carried out in a mixture of organic and inorganic bases.
Organic bases are i.e., pyridines, such as pyridine; substituted pyridines such as dimethyl aminopyridines, or methyl pyridines; or trialkylamines such as triethylamine, diisopropylethylamine, or tributylamine.
Inorganic bases are i.e., carbonates, such as potassium or sodium carbonate and the corresponding hydrogen carbonates.
Therefore, the present invention relates to a process (P6), which is process (P), (P1 ), (PT), (P1 ”), (PT”), (P2), (P2’), (P2”), (P3), (P3’), (P3”), (P4), (P5) or (P5’), wherein the reaction is carried in a mixture of at least one organic base and at least one inorganic base. Therefore, the present invention relates to a process (P6’), which is process (P6), wherein the at least one organic base is chosen from the group consisting of pyridines, substituted pyridines and trialkylamines.
Therefore, the present invention relates to a process (P6”), which is process (P6), wherein the at least one organic base is chosen from the group consisting of pyridine, dimethyl aminopyridines, methyl pyridines, triethylamine, diisopropylethylamine and tributylamine.
Therefore, the present invention relates to a process (P6’”), which is process (P6), wherein the at least one inorganic base is chosen from the group consisting of carbonates and the corresponding hydrogen carbonates.
Therefore, the present invention relates to a process (P6””), which is process (P6), wherein the at least one inorganic base is chosen from potassium carbonate, sodium carbonate and the corresponding hydrogen carbonates.
Usually and preferably, the reaction is carried out at a temperature of between 15-50° C (more preferably at a temperature of between 20-30° C).
Therefore, the present invention relates to a process (P7), which is process (P), (P1 ), (PT), (P1 ”), (PT”), (P2), (P2’), (P2”), (P3), (P3’), (P3”), (P4), (P5), (P5’), (P6), (P6’), (P6”), (P6’”) or (P6””), wherein the reaction is carried out at a temperature of 15 - 50° C.
Therefore, the present invention relates to a process (P7’), which is process (P), (P1 ), (PT), (P1”), (PT”), (P2), (P2’), (P2”), (P3), (P3’), (P3”), (P4), (P5), (P5’), (P6), (P6’), (P6”), (P6’”) or (P6””), wherein the reaction is carried out at a temperature of 20-30° C.
The isolation of the reaction compound (compound of formula (I)) is carried by using commonly known methods. Furthermore, the reaction product of step (i) can be purified. This is also done by commonly known and used methods. Furthermore, the compounds of formula (I) are new.
Therefore, the present invention relates to compounds of formula (I)
Figure imgf000010_0001
wherein R, Ri , R2, R3, R4 Rs, Re R7, Rs and R9 are either
Figure imgf000010_0002
with the proviso that less than 4 substituents are H. (more preferably less than 3 substituents are H, even more less than 2 substituents are H, more preferably wherein none of the substituents are H). The following Examples illustrate the invention further without limiting it. All percentages and parts, which are given, are related to the weight and the temperatures are given in °C, and the pressures are absolute pressures when not otherwise stated.
Examples
Example 1 : Synthesis of 2 '-FL perbutyrate
2'-Fucosyllactose (1.138 g, 2.33 mmol) was placed in a 100 mL 3-necked round-bottom flask under an argon atmosphere. A mixture of pyridine (20.7 ml, 256 mmol) and butyric anhydride (18.0 ml, 107 mmol) was added in one portion. The resulting white turbid mixture was stirred overnight at room temperature.
The reaction mixture was concentrated under reduced pressure. The residue was diluted with dichloromethane and extracted several times with a total 125 of sat. aq. mL NaHCChand once with brine, dried with magnesium sulfate, filtered, and concentrated under reduced pressure. To the residue were added 50 mL of sat. aq. NaHCCh and the mixture was stirred overnight to hydrolyze excess butyric acid. It was then extracted several times with dichloromethane. The combined organic layers were washed with brine, dried with magnesium sulfate, filtered, and concentrated to give 0.46 g of a colorless gum.
The crude product was purified by chromatography (SiC>2, 40-60 micrometer, heptane/ethyl acetate, detected with ELSD). The product was characterized by 1H- and 13C-NMR spectroscopy, IR-spectroscopy, and MS (high resolution).

Claims

Claims
1. Process for producing a compound of formula (I)
Figure imgf000012_0001
wherein R, Ri , R2, R3, R4 Rs, Re R7, Rs and R9 are either
Figure imgf000012_0002
with the proviso that less than 5 substituents are H, characterised in that a compound of formula (II)
Figure imgf000012_0004
is reacted with a compound of formula (III)
Figure imgf000012_0003
wherein X is a halogen atom, -OH or the following moiety O
Figure imgf000013_0001
(* marks the bond to the CO group).
2. Process according to claim 1 , wherein the 2’-FL is reacted with a compound of formula (III)
Figure imgf000013_0002
wherein X is a -Cl, -OH or the following moiety
Figure imgf000013_0003
(* marks the bond to the CO group).
3. Process according to claim 1 , wherein the 2’-FL is reacted with a compound of formula (Illa)
Figure imgf000013_0004
Process according to any of the preceding claims, wherein the compound of formula (I) less than 4 substituents are H.
Process according to any of the preceding claims, wherein the compound of formula (I) less than 3 substituents are H.
6. Process according to any of the preceding claims, wherein the compound of formula (I) less than 2 substituents are H.
Process according to any of the preceding claims, wherein the compound of formula (I) none of the substituents are H.
8. Process according to any of the preceding claims, wherein the reaction is carried out in the presence of at least one polar, basic, inert solvent.
9. Process according to claim 6, wherein the at least one polar, basic, inert solvent is chosen from the group consisting of pyridines, substituted pyridines and trialkylamines.
10. Process according to any of the preceding claims, wherein the compound of formula (III) is used in a molar ratio in regard to compound of formula (II) of 6:1 to 100.
11. Process according to any of the preceding claims, wherein the reaction is carried out at a temperature of 15-50° C.
12. Compounds of formula (I)
Figure imgf000014_0001
wherein
R, Ri , R2, R3, 4 Rs, Re R7, Rs and R9 are either
Figure imgf000014_0002
with the proviso that less than 4 substituents are H.
13. Compounds of claim 12, wherein less than 3 substituents are H.
14. Compounds of claim 12, wherein less than 2 substituents are H.
15. Compounds of claim 12, wherein none of the substituents are H.
PCT/EP2022/082914 2021-12-02 2022-11-23 Synthesis of hmo butyrate WO2023099297A1 (en)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120116065A1 (en) * 2009-04-07 2012-05-10 Glycom A/S Novel method for the synthesis of a trisaccharide
US20140228554A1 (en) * 2011-03-18 2014-08-14 Glycom A/S Synthesis of new fucose-containing carbohydrate derivatives

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120116065A1 (en) * 2009-04-07 2012-05-10 Glycom A/S Novel method for the synthesis of a trisaccharide
US20140228554A1 (en) * 2011-03-18 2014-08-14 Glycom A/S Synthesis of new fucose-containing carbohydrate derivatives

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