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Über die Konstitution von Loroglossin. Vorläufige Mitteilung
Author(s) -
Gray Robert W.,
Guggisberg Armin,
Segebarth Klaus Peter,
Hesse Manfred,
Schmid Hans
Publication year - 1976
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.19760590229
Subject(s) - chemistry , diastereomer , hydrolysis , acetylation , tartrate , absolute configuration , stereochemistry , glucoside , organic chemistry , biochemistry , gene , medicine , alternative medicine , pathology
The Constitution of Loroglossine. Loroglossine, a characteristic constituent of orchids, is shown to be bis‐[4‐(β‐ D ‐glucopyranosyloxy)‐benzyl]‐(2 R , 3 S )‐2‐isobutyl‐tartrate ( 1 ). Hydrolysis and esterification gave 1 mol‐equiv. of dimethyl (+)‐2‐isobutyl‐ erythro ‐tartrate ((+)‐3) and 2 mol.‐equiv. of a glucoside which, after acetylation, gave 4 , identical with a synthetic sample. The erythro configuration of (+)‐ 3 by oxidation of isobutyl‐maleic acid with osmium tetroxide and subsequent esterification. The absolute configuration of (+)‐ 3 was based on Horeau experiments and NMR. data of the diastereomeric mixture of its esters 7 and 8 with S (+)‐ and R (−)‐α‐phenylbutyric acid respectively.