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WO2008034598A8 - Method for the synthesis of hexahydrofuro (2, 3-b) furan-3-ol compounds - Google Patents

Method for the synthesis of hexahydrofuro (2, 3-b) furan-3-ol compounds

Info

Publication number
WO2008034598A8
WO2008034598A8 PCT/EP2007/008148 EP2007008148W WO2008034598A8 WO 2008034598 A8 WO2008034598 A8 WO 2008034598A8 EP 2007008148 W EP2007008148 W EP 2007008148W WO 2008034598 A8 WO2008034598 A8 WO 2008034598A8
Authority
WO
WIPO (PCT)
Prior art keywords
compounds
furan
synthesis
compound
hexahydrofuro
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/EP2007/008148
Other languages
French (fr)
Other versions
WO2008034598A1 (en
Inventor
Peter Jan Leonard M Quaedflieg
Natascha Sereinig
Paulus Lambertus Alsters
Henricus Martinus Ma Straatman
Martin Helmut Friedri Hanbauer
Niek Johannes Ronde
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DSM IP Assets BV
Original Assignee
DSM IP Assets BV
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
Application filed by DSM IP Assets BV filed Critical DSM IP Assets BV
Publication of WO2008034598A1 publication Critical patent/WO2008034598A1/en
Publication of WO2008034598A8 publication Critical patent/WO2008034598A8/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/003—Esters of saturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • 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
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
    • C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Analytical Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention relates to a method for the synthesis of enantiomerically and diastereomerically enriched hexahydro-furo[2,3-b]furan-3-ol compounds by aldol coupling of two suitable O-protected hydroxyaldehydes and subsequent removal of the protecting groups and (optionally simultaneous) cyclization of the resulting aldol compound and subsequent isolation of the desired compounds. The resulting composition can be further diastereomerically enriched through the intermittent acylation or aroylation of the compound and further optionally using a stereoselective hydrolyzing enzyme.
PCT/EP2007/008148 2006-09-19 2007-09-19 Method for the synthesis of hexahydrofuro (2, 3-b) furan-3-ol compounds Ceased WO2008034598A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP06019537.7 2006-09-19
EP06019537 2006-09-19

Publications (2)

Publication Number Publication Date
WO2008034598A1 WO2008034598A1 (en) 2008-03-27
WO2008034598A8 true WO2008034598A8 (en) 2008-05-08

Family

ID=37606835

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2007/008148 Ceased WO2008034598A1 (en) 2006-09-19 2007-09-19 Method for the synthesis of hexahydrofuro (2, 3-b) furan-3-ol compounds

Country Status (1)

Country Link
WO (1) WO2008034598A1 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8921415B2 (en) 2009-01-29 2014-12-30 Mapi Pharma Ltd. Polymorphs of darunavir
EP2327683A1 (en) 2009-11-25 2011-06-01 LEK Pharmaceuticals d.d. Synthesis of acetoxyacetaldehyde
US8829208B2 (en) 2010-01-28 2014-09-09 Mapi Pharma Ltd. Process for the preparation of darunavir and darunavir intermediates
CN102115771B (en) * 2010-09-26 2013-03-13 西南大学 Application of nuclease P1 used as catalyst for direct asymmetrical Aldol reaction between aromatic aldehyde and cyclic ketone
CN111826193A (en) * 2019-04-20 2020-10-27 华东理工大学 A kind of method for preparing cycloalkane from biomass derivatives

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004033462A2 (en) * 2002-10-09 2004-04-22 The Board Of Trustees Of The University Of Illinois METHOD OF PREPARING (3R, 3aS, 6aR) -3- HYDROXYHEXAHYDROFURO [2, 3-b] FURAN AND RELATED COMPOUNDS
AU2003275675A1 (en) * 2002-12-27 2004-07-29 Sumitomo Chemical Company, Limited Process for producing hexahydrofurofuranol derivative, intermediate thereof and process for producing the same
ES2372417T3 (en) * 2005-06-06 2012-01-19 Sumitomo Chemical Company Limited METHOD TO PRODUCE A HEXAHYDROFUROFURANOL DERIVATIVE.

Also Published As

Publication number Publication date
WO2008034598A1 (en) 2008-03-27

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