1.
Carbohydr Res
; 239: 197-207, 1993 Feb 01.
Article
in English
| MEDLINE
| ID: mdl-8457995
ABSTRACT
The order of esterification of the eight hydroxyl groups of alpha,alpha-trehalose is HO-6.6' > HO-2.2' > HO-3.3' > HO-4.4'. Under the appropriate conditions of benzoylation, the heptabenzoate with HO-4' free was obtained in good yield (58%), along with the octabenzoate and the hexabenzoate having HO-4.4' free. The readily isolated heptabenzoate was a convenient starting material for the synthesis of 4-azido-4-deoxy- (84%) and 4-amino-4-deoxy-alpha-D-galactopyranosyl alpha-D-glucopyranoside, and the heptabenzoate of alpha-D-galactopyranosyl alpha-D-glucopyranoside with HO-4' free, which was used as a synthetic precursor of 4-azido-4-deoxy-alpha-D-glucopyranosyl alpha-D-glucopyranoside and its amino analogue.
Subject(s)
Azides/chemical synthesis , Trehalose/analogs & derivatives , Carbohydrate Sequence , Isomerism , Molecular Sequence Data , Trehalose/chemical synthesis
2.
Carbohydr Res
; 240: 287-93, 1993 Feb 24.
Article
in English
| MEDLINE
| ID: mdl-8458011