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3‐O‐Methl‐6‐desoxy‐ L ‐talose, Synthese und Identifizierung mit L ‐Acovenose. Desoxyzucker, 43. Mitteilung
Author(s) -
Kapur B. M.,
Allgeier H.
Publication year - 1968
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.19680510110
Subject(s) - chemistry , sodium periodate , hydrolysis , periodate , stereochemistry , organic chemistry
3‐O‐methly‐6‐deoxy‐ L ‐talose has been synthesized starting from 1, 2–5, 6‐di‐O‐isopropylidene‐α‐ D ‐allose ( 1 ). Methylation, selective acidic hydrolysis, sodium periodate oxidation and G RIGNARD reaction with CH 3 MgBr gave a mixture of the 1, 2‐isopropylidene derivatives of 3‐O‐methyl‐6‐deoxy‐ D ‐allose and 3‐O‐methyl‐6‐deoxy‐ D ‐allose ( 7 ) and 3‐O‐methyl‐6‐deoxy‐ L ‐talose ( 8 ) ( L ‐acovenose) could be obtained. Oxidation of the latter gave the corresponding crystalline lactone, which could be indentified with a sample obtained from natural L ‐acovenose.