WO2010004269A3 - Synthèse stéréospécifique - Google Patents

Synthèse stéréospécifique Download PDF

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Publication number
WO2010004269A3
WO2010004269A3 PCT/GB2009/001684 GB2009001684W WO2010004269A3 WO 2010004269 A3 WO2010004269 A3 WO 2010004269A3 GB 2009001684 W GB2009001684 W GB 2009001684W WO 2010004269 A3 WO2010004269 A3 WO 2010004269A3
Authority
WO
WIPO (PCT)
Prior art keywords
deoxyidonojirimycin
deoxynojirimycin
acid derivatives
stereospecific synthesis
iduronic acid
Prior art date
Application number
PCT/GB2009/001684
Other languages
English (en)
Other versions
WO2010004269A2 (fr
Inventor
Alexander Charles Weymouth-Wilson
George W. J. Fleet
Original Assignee
Dextra Laboratories Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from GB0812613A external-priority patent/GB0812613D0/en
Priority claimed from GB0812609A external-priority patent/GB0812609D0/en
Priority claimed from GB0812605A external-priority patent/GB0812605D0/en
Application filed by Dextra Laboratories Limited filed Critical Dextra Laboratories Limited
Publication of WO2010004269A2 publication Critical patent/WO2010004269A2/fr
Publication of WO2010004269A3 publication Critical patent/WO2010004269A3/fr

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/02—Preparation by ring-closure or hydrogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
    • C12P17/181—Heterocyclic compounds containing oxygen atoms as the only ring heteroatoms in the condensed system, e.g. Salinomycin, Septamycin

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Molecular Biology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un procédé de préparation d’un composé de formule générale (IV) dans laquelle OX, R3 et R3’ sont tels que définis dans le présent document; et l’utilisation de composés de formule générale (IV) en tant qu’intermédiaires dans des procédés de synthèse stéréospécifique de molécules biologiquement actives.
PCT/GB2009/001684 2008-07-10 2009-07-07 Synthèse stéréospécifique WO2010004269A2 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
GB0812613A GB0812613D0 (en) 2008-07-10 2008-07-10 Process for the preparation of 1-deoxyidonojirimycin
GB0812605.4 2008-07-10
GB0812609A GB0812609D0 (en) 2008-07-10 2008-07-10 Process for the preparation of deoxynojirimycin
GB0812609.6 2008-07-10
GB0812613.8 2008-07-10
GB0812605A GB0812605D0 (en) 2008-07-10 2008-07-10 Process for preparation of iduronic acid

Publications (2)

Publication Number Publication Date
WO2010004269A2 WO2010004269A2 (fr) 2010-01-14
WO2010004269A3 true WO2010004269A3 (fr) 2010-11-18

Family

ID=41256095

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2009/001684 WO2010004269A2 (fr) 2008-07-10 2009-07-07 Synthèse stéréospécifique

Country Status (1)

Country Link
WO (1) WO2010004269A2 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3035787B1 (fr) * 2015-05-07 2018-08-24 L'oreal Procede de traitement des matieres keratiniques a partir de derives de c-glycosides amides, acides ou ester, et la composition cosmetique les contenant

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0359263A2 (fr) * 1988-09-16 1990-03-21 Merrell Dow Pharmaceuticals Inc. Synthèse d'intermédiaire pour la préparation de nojirimycine et dérivés semblables

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0359263A2 (fr) * 1988-09-16 1990-03-21 Merrell Dow Pharmaceuticals Inc. Synthèse d'intermédiaire pour la préparation de nojirimycine et dérivés semblables

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
A. KLEMER ET AL: "Eine neue Synthese von 5-Amino-5-desoxy-1,2-isopropyliden-alpha-D-glucofuranose", CARBOHYDRATE RESEARCH, vol. 68, 1979, pages 391 - 395, XP002558145 *
BASHYAL B P ET AL: "THE SYNTHESIS OF POLYHYDROXYLATED AMINO ACIDS FROM GLUCURONOLACTONE ENANTIOSPECIFIC SYNTHESES OF 2S 3R 4R 5S TRIHYDROXYPIPECOLIC ACID 2R 3R 4R 5S TRIHYDROXYPIPECOLIC ACID AND 2R 3R 4R DIHYDROXYPROLINE", TETRAHEDRON, vol. 43, no. 2, 1987, pages 415 - 422, XP002556804, ISSN: 0040-4020 *
BYONG WON LEE ET AL: "A short and efficient synthesis of 2R,3R,4R-3,4-dihydroxyproline,1,4- dideoxy-1,4-imino-L-xylitol,2R,3R,4R,5S-3,4 ,5-trihydroxypipecolic acid, and 1,5-dideoxy-1,5-imino-L-iditol", SYNTHESIS 2000 DE, no. 9, 2000, pages 1305 - 1309, XP002558146, ISSN: 0039-7881 *
GREEN T W; WUTS P G M: "Greene's Protective Groups in Organic Synthesis (Fourth Edition)", 10 April 2006, NEW YORK, WILEY & SONS, US, XP002558147 *
INGOLF MACHER, KARL DAX, HARTMUT INSELSBACHER, HANS WEIDMANN, CARBOHYDRATE RESEARCH, vol. 77, no. 1, 1979, pages 225 - 230, XP002556806 *
OJEDA R ET AL: "A new route to L-iduronate building-blocks for the synthesis of heparin- like oligosaccharides", SYNLETT 1999 DE, no. 8, 1999, pages 1316 - 1318, XP009126136, ISSN: 0936-5214 *

Also Published As

Publication number Publication date
WO2010004269A2 (fr) 2010-01-14

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