Premium
Analogues de la lincomycine. I. Allongement de la chaîne du di‐ O ‐isopropylidène‐1,2:3,4‐α‐ D ‐galacto‐hexodialdopyrannose‐1,5
Author(s) -
Tronchet Jean M. J.,
Massoud Mohammed A. M.
Publication year - 1979
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19790620530
Subject(s) - chemistry , wittig reaction , malonic acid , reagent , stereochemistry , pyranose , chain (unit) , betaine , organic chemistry , physics , astronomy
Lincomycin analogues. I. Chain‐extensions of [1,2:3,4]‐di‐ O ‐isopropylidene‐α‐ D ‐galacto‐hexodialdo‐1,5‐pyranose The title aldehydosugar 1 treated with Wittig reagents led in good to excellent yields to the unsaturated sugar derivatives 3–7 and 10–15, 8 having been prepared by condensation of 1 with malonic acid. The configuration ( Z or E ) of each compound obtained has been established by 1 H‐NMR. These chain‐extensions constitute the first synthetic step towards the preparation of lincomycin analogues.