Synthesis of higher sugars as precursors for the synthesis of chiral polyhydroxylated macrocyclic lactones
Author(s) -
Momčilo Miljković,
Margaret Habash-Marino
Publication year - 2000
Publication title -
journal of the serbian chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.227
H-Index - 45
eISSN - 1820-7421
pISSN - 0352-5139
DOI - 10.2298/jsc0007497m
Subject(s) - chemistry , hydroxymethyl , wittig reaction , carbohydrate , organic chemistry , stereochemistry , coupling reaction , combinatorial chemistry , catalysis
A general method for the synthesis of higher sugars that can be used as precursors for the synthesis of polyhydroxylatedmacrocyclic lactones (macrolides) was described. The extension of the carbohydrate chain of a hexopyranose was effected at its C(6) hydroxymethyl carbon by coupling of two carbohydrate precursors via Wittig reaction. In this way 6,7-dideoxy-2,3,4,5,8,9,10-hepta-O-methyl-11-O-triphenylmethyl-D-arabino-D-glucoundecanose diethyl dithioacetal (1) was synthesized as a model compound.
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