CN110283047A - The synthetic method of monosaccharide moieties methylation Alday alcohol acetic ester - Google Patents
The synthetic method of monosaccharide moieties methylation Alday alcohol acetic ester Download PDFInfo
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- CN110283047A CN110283047A CN201910625903.1A CN201910625903A CN110283047A CN 110283047 A CN110283047 A CN 110283047A CN 201910625903 A CN201910625903 A CN 201910625903A CN 110283047 A CN110283047 A CN 110283047A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
Abstract
The invention discloses the synthetic methods of monosaccharide moieties methylation Alday alcohol acetic ester, belong to the synthesis field of monosaccharide moieties methylation, and the synthetic method, which includes: (1), to be carried out reduction reaction for monosaccharide and generate corresponding Alday alcohol product；(2) the Alday alcohol product obtained after reduction reaction carries out partial methylation reaction；(3) by partial methylation reaction product carry out acetylization reaction to get.Compared to existing five step synthetic method, three step synthetic methods of the invention can be with partial methylation Alday alcohol acetic ester class compound that simultaneously synthesizing furans and pyranoid form are all levied, the methylation reaction time is effectively shortened simultaneously, is methylated hydroxyl more quickly；Compared to the identical methylation time, three step synthetic methods of the invention significantly improve peak response value, have many advantages, such as that synthesis step is few, intensity is high, quantity is more, yield is high, simple and quick.
Description
Technical field
The present invention relates to the synthetic methods of monosaccharide moieties methylation Alday alcohol acetic ester, belong to the partial methylation of monosaccharide
Field.
Background technique
At present to the partial methylation research of monosaccharide it has been reported that existing synthetic route needs the preparation of five step synthetic routes
The partial methylation Alday alcohol acetic ester derivative of neutral sugar, it may be assumed that hydrochloric acid methanol solution → partial methylation → hydrolysis → reduction
→ acetylation → PMAAs.
That there are synthesis steps is more for five step synthetic methods of the partial methylation of existing monosaccharide, intensity is weak, synthetic product quantity
Less, the defects of low yield, have much room for improvement.
Summary of the invention
The object of the present invention is to provide a kind of synthetic methods of new monosaccharide methylation Alday alcohol acetic ester derivative；
Above-mentioned purpose of the invention is achieved through the following technical solutions:
A kind of synthetic method of monosaccharide moieties methylation Alday alcohol acetic ester, comprising the following steps:
(1) monosaccharide is subjected to reduction reaction and generates corresponding Alday alcohol product；
(2) the Alday alcohol product obtained after reduction reaction carries out partial methylation reaction；
(3) by partial methylation reaction product carry out acetylization reaction to get.
Wherein, heretofore described monosaccharide is preferably neutral sugar, including but not limited to glucose, galactolipin, mannose,
Rhamnose, arabinose, xylose or ribose etc.；The monosaccharide can be with pyranoid form or galactofuranosylceramides.
If her pyranoid form or galactofuranosylceramides are substrate, the galactolipin PMAAs derivative of series is synthesized；Original synthesis
Method (five step synthetic methods) is only capable of obtaining 15 kinds of PMMAs derivatives, and the method for the present invention can obtain 21 kinds of portions of whole features
Divide methylation galactitol acetic ester derivative；By the same manner, common synthetic methods are at best able to respectively obtain 15 kinds of sweet dews
Sugar and glucose PMMAs derivative, synthetic method of the present invention can respectively obtain 23 kinds of partial methylation mannoses and glucose
PMAAs derivative；
If common synthetic methods are only capable of obtaining 7 kinds of PMMAs derivatives using the methyl five-carbon ring aldehydo sugar such as rhamnose as substrate,
The method of the present invention can obtain 11 kinds of PMAAs derivatives of rhamnose of whole features；
If common synthetic methods can be only respectively synthesized using the five-carbon ring aldehydos such as arabinose, xylose, ribose sugar as substrate
To 7 kinds of PMMAs derivatives of corresponding monosaccharide, the method for the present invention can be respectively synthesized to obtain corresponding 11 kinds, 10 kinds and 10 kinds of PMMAs
Derivative.
Reduction reaction described in step (1) preferably obtains corresponding alcohols using deuterated sodium borohydride reduction monosaccharide and produces
Object.
Partial methylation described in step (2) reaction include: the alcohol product that will be obtained after reduction reaction be dissolved in it is organic
Partial methylation is carried out with iodomethane in solvent to react；It is furthermore preferred that the alcohol product obtained after reduction reaction is dissolved in diformazan
In base sulfoxide solution or n,N-Dimethylformamide, BaO, Ba (OH) is added28H2O and iodomethane carry out partial methylation reaction.
Acetylization reaction described in step (3) is preferred are as follows: by partial methylation reaction product and pyridine and acetic anhydride
Carry out acetylization reaction.
The reduction and part methyl of three step synthetic methods of the invention using a variety of common monosaccharides as starting material, by starting material
Change and acetylation three-step reaction, synthesis episode methylation Alday alcohol acetic ester derivative are closed compared to existing five step
At method, three step synthetic methods of the invention can be with partial methylation Alday alcohol second that simultaneously synthesizing furans and pyranoid form are all levied
Acid esters compound；The methylation reaction time is effectively shortened simultaneously, is methylated hydroxyl more quickly；Compare identical first
Base time, three step synthetic methods of the invention significantly improve peak response value；The method of the present invention have synthesis step is few, intensity is high,
Many advantages, such as quantity is more, yield is high, simple and quick.
It is of the invention main the utility model has the advantages that
Firstly, using three step synthetic methods of the invention, no matter using galactopyranose or galactofuranosylceramides the bottom of as
Object, the PMMAs derivative that can synthesize series can obtain 21 kinds of partial methylation monosaccharide PMMAs derivatives.Using the present invention
Episode methylation Alday alcohol acetic ester derivative is prepared in three step synthetic methods, and the PMMAs of all synthesis is derivative
Object is new compound, has the advantages such as yield is high, intensity is high, quantity is more, synthesis step is few.
Secondly, three step synthetic methods creativeness of the invention simplifies the tedious steps for preparing PMMAs, the synthetic is simultaneously
Characteristic compounds with furanose and pyranose whole feature structure.
Finally, due to the difference of sugar alcohol and monosaccharide structure and space structure, three step synthetic methods of the invention are effectively shortened
The methylation reaction time, it is methylated hydroxyl more quickly.Three step synthetic methods of the invention are easy, quickly, it is accurate, have
Effect, yield are high, intensity is high, quantity is more, synthesis step is few, can be used for the research of polysaccharide connection type.
Detailed description of the invention
Fig. 1 is using pyranoid ring or furan nucleus galactolipin as substrate reduction → partial methylation → PMMAs synthetic route.
Fig. 2 compares new and old synthetic method to synthesis partial methylation Alday alcohol acetic ester derivative by taking galactolipin as an example
GC-MS total ion current figure.
Fig. 3 galactolipin difference methylation Alday alcohol acetic ester GC-MS total ion current figure.
Fig. 4 compound 81H-NMR and13C-NMR figure.
Specific embodiment
Further describe the present invention below in conjunction with specific embodiment, the advantages and features of the present invention will be with description and
It is apparent.But examples are merely exemplary for these, and it is not intended to limit the scope of the present invention in any way.Those skilled in the art
Member it should be understood that can modify without departing from the spirit and scope of the invention to details and form of the invention or
Replacement, but these modifications and replacement are fallen within the protection scope of the present invention.
As shown in table 1, for three step synthetic methods of the invention using a variety of common monosaccharides as starting material, monosaccharide can be glucose, half
The neutral sugars such as lactose, mannose, rhamnose, arabinose, xylose, ribose pass through the reduction of starting material and partial methylation etc.
Reaction, synthesis episode methylation Alday alcohol acetic ester derivative, the PMAAs that wherein five-carbon ring aldehydo sugar and six carbon aldoses synthesize
Derivative quantity is different, and is analyzed by gas chromatograph-mass spectrometer PMAAs derivative
1 episode methylated monosaccharides PMMP derivative situation of table
Instrument and reagent
7980A-5975C gas chromatograph-mass spectrometer (Agilent company, the U.S.)；(Beijing is long for HH521-4 electric-heated thermostatic water bath
Pacify scientific instrument factory)；FA2104 electronic analytical balance (Shanghai balance factory)；Christ LDplus freeze drier (is thought to reach in Beijing
Industrial Instrument Ltd.)；GENLVS centrifuge (Changsha Xin Ao instrument and meter Co., Ltd)；N-1100V-W (WD) rotation
Evaporimeter (Tokyo is physical and chemical).Pyridine (development in science and technology Co., Ltd is recovered in Tianjin)；(Tianjin is into the limited public affairs of Feng Huagong for acetic anhydride
Department)；Sodium borohydride (Sinopharm Chemical Reagent Co., Ltd.)；Inositol (Shanghai Blue Season Technology Development Co., Ltd)；Trifluoro second
Acid (fine chemistry industry research institute is recovered in Tianjin)；Dimethyl sulfoxide (Tianjin Fu Yu Fine Chemical Co., Ltd).
The methylation Alday alcohol acetic ester derivative synthesis of 1 galactose moiety of embodiment and 1 synthetic method of analysis
1.1 deuterated sodium borohydride reductions
Galactolipin 5g is taken, the deuterated sodium borohydride of 1g is separately added into, 100ml water, 2h is set in room temperature decentralization after oscillation, makes galactolipin
It is reduced into corresponding galactitol.It instills glacial acetic acid and decomposes excessive deuterated sodium borohydride, until bubble-free generates.Solution exists
50 DEG C are concentrated to dryness.0.1% methanol hydrochloride solution is added, is evaporated to dryness under reduced pressure for 50 DEG C, is repeated 5 times to remove boron after oscillation
Acid group.
1.2 partial methylations and acetylation
The galactitol of above-mentioned reduction is dissolved in dimethyl sulphoxide solution, BaO, Ba (OH) is then added28H2O, iodomethane,
Rotor low temperature dark place in magnetic stirring apparatus is added to be vigorously stirred, filters, above-mentioned dried Sheng is added in pyridine and acetic anhydride
In the reaction flask for having sugared residue, overnight, 5 times of amount water stopped reactions are added to get the galactitol acetic acid esters for arriving partial methylation
Derivative.
2. composite result
Three step synthetic methods of the invention are compared with five original step synthetic methods, using deuterated sodium borohydride reduction, simply
Quickly, high-efficient, synthesis step is few: neutral sugar first reduction → partial methylation → PMMAs (Fig. 1).With common synthetic methods phase
Than (Fig. 2A and B), the PMMAs class compound peak number that three step synthetic methods of the invention obtain is more, intensity is high.
The analysis of galactose moiety methylation Alday alcohol acetic ester derivative
As shown in Fig. 2 total ion current figure, using galactolipin as substrate, it is practical that theory synthesizes 21 kinds of galactolipin PMMAs derivatives
15 kinds of PMMAs derivatives are synthesized, and common synthetic methods are theoretically synthesized practical 7 kinds of the synthesis of 15 kinds of PMMAs derivatives.In 15-
When 20min, there are 4 peaks in commonsense method, and 1,2, No. 3 peak intensity is very low, retention time close to being difficult to distinguish, and new method 2,3,
The intensity at No. 4 peaks is 50,35,75 times of corresponding 2,3, No. 4 peaks of commonsense method respectively；In 20-25min, commonsense method goes out
Existing 3 peaks, intensity is low, and retention time is close to be difficult to distinguish, and 11 peaks, not closing including commonsense method occurs in new method
At 6,7,8,9,10,12,13, No. 14 peaks, No. 11 in new method, No. 15, peak intensity be corresponding commonsense method 6,7 respectively
70,20 times of number peak.By the comparison of total ion figure it can be found that new method has very big promotion in peak intensity, quantity.In order to
Further the synthesized galactolipin PMMAs derivative of confirmation has synthesized success, is further detected by GC-MS as shown in Figure 2 B,
Wherein the GC-MS mass spectrometric data of compound 11 and compound 12 is shown, main fragment ion m/z 261,189,161,129,
117,101,87 and 59 abundance is higher, methylates Alday alcohol acetic ester derivative (Fig. 3-A) for 1 methoxy moieties；Chemical combination
The GC-MS mass spectrometric data of object 9 shows that the abundance of main fragment ion m/z 233,189,129,101,87 and 59 is higher, is 2
Methoxy moieties methylate Alday alcohol acetic ester derivative (Fig. 3-B)；The main fragment fragment ion of compound 5 is respectively m/
Wherein m/z 117 is typical trimethoxy partial methylation Alday alcohol acetic acid to z 189,161,129,117,101,87 and 59
Ester derivant (Fig. 3-C)；The main fragment fragment ion of compound 1 is m/z 205,189,161,145,129,117,101,87
And 59 wherein two methoxyl group scission fragments ions between typical C3 and C4 of m/z 161,205, it is accredited as tetramethoxy part
It methylates Alday alcohol acetic ester derivative (Fig. 3-D).
The methylation Alday alcohol acetic ester derivative synthesizing process validity confirmatory test of 1 galactose moiety of test example
For the feasibility for further confirming synthetic method, the galactose moiety methylation Alday alcohol synthesized with embodiment 1
Nmr analysis is carried out for acetic ester derivative compound 8 confirms structure:
Compound 81H-NMR(CD3OD, 400Hz) in spectrum (figure .4A), it can be observed 4 at low field δ 1.5-2.5
Acetyl protons signal, respectively δ 2.01 (3H), 2.01 (3H), 2.02 (3H) and 2.11 (3H).The observable at δ 3.0-4.5
To 2 methoxy proton signals, respectively δ 3.29 (3H), 3.43 (3H).According to galactose moiety methylation Alday alcohol acetic acid
Ester structure feature speculates that compound 8 is the hexose alcohol acetic ester derivative connected there are four two methoxyl groups of acetyl group.With GC-
MS database compares 8 structure of compound and matches.According to compound 813C-NMR composes (Fig.4B), it can be seen that 4 acetyl group
Proton signal, respectively δ 171.61,171.90,172.19 and 172.37.6 skeleton carbons and two methyl proton signals, respectively
For δ 59.28,61.23,64.08,70.25,70.72,71.10,72.14 and 78.86.
Compound 81H-1In H COSY spectrum, it may be observed that 1,2,4,5-tera-O-acetyl-3,6-di-O-methyl-
The H-1 (δ H4.40,4.15) and H-2 (δ H5.22), H-2 and H-3 (δ H3.61), H-3 and H-4 (δ of D-galactitol
H5.15), the relevant peaks of H-4 and H-5 (δ H5.31), H-5 and H-6 (δ H3.38).The hsqc spectrum of compound 8 is incorporated in it is found that can
Observe the coherent signal of 6 apparent hydrogen and carbon.The carbon signal at hydrogen signal and δ 63.6 i.e. at δ 4.40 exists obvious
Relevant peaks；There are apparent relevant peaks for the carbon signal at hydrogen signal and δ 71.1 at δ 5.22；In δ 3.61,5.15,5.31
With 3.38 at hydrogen signal there are apparent relevant peaks with the carbon signal at δ 78.8,70.2,70.7 and 72.1 respectively.
In the HMBC spectrum of compound 8 it is found that 4.40 (dd, 11.64,5.72) and 4.15 (dd, and δ 11.64,5.76)
C78.8 (C-3), δ C172.37 (OAc) are related, illustrate that acetyl group links C-1.5.22 (dt, 5.72,2.32) with δ C70.2
(C-4), δ C171.61 (OAc) is related, illustrates that acetyl group links C-2.3.61 (dd, 9.12,2.36) with δ C63.6 (C-1), δ
C70.7 (C-5) is related.5.15 (dd, 9.08,2.08) with δ C71.1 (C-2), δ C72.1 (C-6), δ C171.19 (OAc) are related,
Illustrate that acetyl group links C-4.5.31 (dt, 5.88,2.08) with δ C78.8 (C-3), δ C171.90 (OAc) is related, illustrates second
Acyl group links C-5.3.38 (m) is related to δ 70.2 (C-4).
To sum up, authenticating compound 8 be 1,2,4,5-tera-O-acetyl-3,6-di-O-methyl-D-galactitol,
Galactolipin glucosides key connection type is → 2,4)-Galp- (1 →.
The comparative analysis of the 2 new and old synthetic method of gala carbohydrates and their derivative of test example is tested
By three step synthetic methods (embodiment 1) of partial methylation Alday alcohol acetic ester derivative of the invention with it is original
Synthetic method (five step synthetic methods: hydrochloric acid methanol solution → partial methylation → hydrolysis → reduction → acetylation → PMAAs) comparison
It was found that: three step synthetic method synthesis steps of the invention are few, intensity is high, quantity is more, yield is high, simple and quick, while the present invention three
Step synthetic method shortens the methylation reaction time, is methylated hydroxyl more quickly.And when comparing identical methylation
Between, three step synthetic methods of the invention significantly improve peak response value.
Claims (9)
1. a kind of synthetic method of monosaccharide moieties methylation Alday alcohol acetic ester, comprising the following steps:
(1) monosaccharide is subjected to reduction reaction and generates corresponding Alday alcohol product；
(2) the Alday alcohol product obtained after reduction reaction carries out partial methylation reaction；
(3) by partial methylation reaction product carry out acetylization reaction to get.
2. synthetic method described in accordance with the claim 1, which is characterized in that the monosaccharide is neutral sugar.
3. synthetic method described in accordance with the claim 1, which is characterized in that the neutral sugar include but is not limited to glucose,
Galactolipin, mannose, rhamnose, arabinose, xylose or ribose.
4. synthetic method described in accordance with the claim 3, which is characterized in that the monosaccharide can be pyranoid form or furan type gala
Sugar.
5. synthetic method described in accordance with the claim 1, which is characterized in that reduction reaction described in step (1) is using deuterated
Sodium borohydride reduction monosaccharide obtains corresponding Alday alcohol product.
6. synthetic method described in accordance with the claim 1, which is characterized in that the reaction packet of partial methylation described in step (2)
It includes: the Alday alcohol product obtained after reduction reaction being dissolved in organic solvent and is reacted with iodomethane progress partial methylation.
7. synthetic method described in accordance with the claim 1, which is characterized in that the organic solvent includes but is not limited to dimethyl
Sulfoxide solution or n,N-Dimethylformamide.
8. synthetic method according to claim 7, which is characterized in that the reaction packet of partial methylation described in step (2)
It includes: the Alday alcohol product obtained after reduction reaction being dissolved in organic solvent, BaO is added, Ba (OH)28H2O and iodomethane into
The reaction of row partial methylation.
9. synthetic method described in accordance with the claim 1, which is characterized in that acetylization reaction described in step (3) are as follows: by portion
Methylation reaction product and pyridine and acetic anhydride is divided to carry out acetylization reaction.
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