Enantioselective Synthesis of Methylfuranosides of Unnatural 3,6‐Dideoxy‐3‐methylaldohexoses from Lactates by Homoaldol Reactions | Zendy

Hoppe Dieter | Zendy; Tarara Gerhard | Zendy; Wilckens Marcus | Zendy; Jones Peter G. | Zendy; Schmidt Dieter | Zendy; Stezowski John J. | Zendy

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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.

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