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The Total Synthesis of C‐Glycosides with Completely Resolved Seven‐Carbon Backbone Polyol Stereochemistry: Stereochemical Correlations and Access to L ‐Configured and Other Rare Carbohydrates
Author(s) -
Hoffmann H. Martin R.,
Dunkel Ralf,
Mentzel Matthias,
Reuter Henning,
Stark Christian B. W.
Publication year - 2001
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20011119)7:22<4771::aid-chem4771>3.0.co;2-j
Subject(s) - polyol , chemistry , stereoselectivity , stereochemistry , desymmetrization , hydroxylation , hydroxymethyl , glycoside , molecule , organic chemistry , enantioselective synthesis , catalysis , polyurethane , enzyme
The de novo synthesis of a full set of hydroxymethyl C‐glycosides from only two precursors is described. The seven‐carbon target molecules contain five stereocentres and bridge the stereochemical gap between natural D ‐configured and non‐natural L ‐configured series of hexoses. Key steps include hydroxylation, differential protection, stereoselective reduction and desymmetrization of 8‐oxabicyclo[3.2.1]oct‐6‐enes. C‐Terminus differentiation and C‐terminus excision of the seven‐carbon polyol backbone lead to hexoses, including those of the L ‐series. A stereochemical and genetic classification of C‐glycosides is presented.