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Synthese von β‐ D ‐Glucopyranosiden einiger hydroxylierter Vitamin‐D‐Verbindungen
Author(s) -
Fürst Andor,
Labler Ludvik,
Meier Werner
Publication year - 1983
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.19830660720
Subject(s) - chemistry , glucoside , vitamin , yield (engineering) , stereochemistry , vitamin d and neurology , acetylation , substrate (aquarium) , isomerization , glycoside , calcitriol , trisaccharide , disaccharide , organic chemistry , catalysis , biochemistry , calcium , medicine , materials science , alternative medicine , oceanography , pathology , geology , metallurgy , gene , endocrinology
Synthesis of β‐ D ‐Glucopyranosides of some Hydroxylated Vitamin‐D Compounds Cholesta‐5, 7‐diene‐1α, 3β‐diol (1a) was glycosylated with ‘α‐acetobromoglucose’ (2) as well as with ‘α‐acetobromocellobiose’ (4) to yield the 3‐(glycosides) 1b and 1c , respectively. Irradiation of these products with UV light followed by thermal isomerization led to the corresponding vitamin‐D derivatives 3a and 3c. Direct glucosylation of vitamin D 3 (3f) and vitamin D 2 (5a) with 2 gave the derivatives 3g and 5b , respectively. With 25‐hydroxycholecalciferol ( = calcidiol; 6a ) as substrate, besides the 3‐(glucoside) 6b small amounts of the C(25)‐analog 6c were formed. The reaction of 1α, 25‐dihydroxycholecalciferol ( = calcitriol; 6e ) with 2 furnished the 3‐ and the 1‐(glucoside) ( 6f and 6g , respectively) as the major components and the C(25)‐analog 6h in minor quantity. From the acetylated 3‐(glucosides) 3a, 3g, 5b, 6b , and 6f , the free glucopyranosides 3b, 3h, 5c, 6d , and 6i , respectively, were prepared as well as the free glucopy‐ranosyl‐glucopyranoside 3d from the acetylated disaccharide 3c.