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Synthesis of Long‐Chain Sugars by Iterative, Diastereoselective Homologation of 2,3‐ O ‐Isopropylidene‐ D ‐glyceraldehyde with 2‐Trimethylsilylthiazole
Author(s) -
Dondoni Alessandro,
Fantin Giancarlo,
Fogagnolo Marco,
Medici Alessandro
Publication year - 1986
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.198608351
Subject(s) - glyceraldehyde , chain (unit) , chemistry , stereochemistry , computer science , combinatorial chemistry , organic chemistry , physics , astronomy , dehydrogenase , enzyme
D ‐Aldoses with up to nine C atoms have been synthesized stepwise by homologation of the glyceraldehyde derivative 1 . The two key steps are the anti diastereoselective addition of 2 to an α‐chiral aldehyde and the conversion of the thiole ring in the adduct into the formyl group. The reaction sequence 1+2→3→4 illustrates the principle of the reaction.