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An improved synthesis of 4-azido-4-deoxy- and 4-amino-4-deoxy-α,α-trehalose and their epimers

✍ Scribed by Rafik W. Bassily; Ramadan I. El-Sokkary; Basim Azmy Silwanis; Asaad S. Nematalla; Mina A. Nashed

Publisher: Elsevier Science
Year: 1993
Tongue: English
Weight: 826 KB
Volume: 239
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(93)84215-r

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✦ Synopsis

The order of esterification of the eight hydroxyl groups of cu,cY-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-deoxyiY-o-galactopyranosyl a-o-glucopyranoside, and the heptabenzoate of a-o-galactopyranosyl a-o-glucopyranoside with HO-4' free, which was used as a synthetic precursor of 4-azido-4-deoxy-a-o-glucopyranosyl cu-o-glucopyranoside and its amino analogue.

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