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Enantioselective Synthesis of Methylfuranosides of Unnatural 3,6‐Dideoxy‐3‐methylaldohexoses from Lactates by Homoaldol Reactions
Author(s) -
Hoppe Dieter,
Tarara Gerhard,
Wilckens Marcus,
Jones Peter G.,
Schmidt Dieter,
Stezowski John J.
Publication year - 1987
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198710341
Subject(s) - enantioselective synthesis , chemistry , sequence (biology) , stereochemistry , group (periodic table) , organic chemistry , catalysis , biochemistry
A three‐step sequence—homoaldol reaction, epoxidation, methanolysis —can be employed to extend ( S )‐2‐benzyloxypropanal 1 by one 2‐hydroxy‐3‐methylpropanal unit. This method provides a general route to unnatural 3‐deoxy‐3‐methylaldoses in the form of anomerically pure methylfuranosides such as 2 bearing a free 2‐hydroxyl group.