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Synthesis of L ‐ and D ‐4,6‐Dideoxyhexoses and 4,6‐Dideoxy‐ C ‐phenylglycosides from Enzyme‐Generated Products
Author(s) -
Acetti Daniela,
Brenna Elisabetta,
Fuganti Claudio,
Gatti Francesco G.,
Malpezzi Luciana,
Serra Stefano
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800662
Subject(s) - chemistry , intramolecular force , moiety , double bond , epoxide , stereochemistry , ring (chemistry) , oxidative cleavage , cleavage (geology) , bond cleavage , optically active , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
Optically active 1,3‐diols 1 were prepared by biocatalysed routes. The synthetic versatility of compounds 1 as chiral building blocks was shown. The oxidative cleavage of the double bond afforded a carbonyl moiety, which allowed for elongation by Grignard addition and further derivatisation to make deoxy sugars readily available. The epoxidation of the same double bond allowed the direct intramolecular opening of the epoxide ring to generate deoxy C ‐phenylglycosides. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)