SYNTHESIS OF TRIDEUTERIOMETHYL 5-DEUTERIUM-BETA-D-MANNOPYRANOSIDE

Authors
GODDAT J DATTA P GREY AA CARVER JP SHAH RN
Citation
J. Goddat et al., SYNTHESIS OF TRIDEUTERIOMETHYL 5-DEUTERIUM-BETA-D-MANNOPYRANOSIDE, Journal of carbohydrate chemistry, 12(6), 1993, pp. 793-800
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology
Journal title
Journal of carbohydrate chemistry → ACNP
ISSN journal
07328303
Volume
12
Issue
6
Year of publication
1993
Pages
793 - 800
Database
ISI
SICI code
0732-8303(1993)12:6<793:SOT5>2.0.ZU;2-Q
Abstract
The title compound was prepared by first converting trideuteriomethyl 2,3,4-tri-O-benzyl-beta-D-mannopyranoside to a 6-bromo-6-deoxy derivat ive which on elimination by using DBU (1,8-diazabicyclo5.4.0!undec-7- ene) or DBN (1,5-diazabicyclo4.3.0!non-5-ene) gave a hex-5-enopyranos ide derivative. The deuteroboration of the hex-5-enopyranoside followe d by oxidation and subsequent deblocking produced trideuteriomethyl 5- deuterium-beta-D-mannopyranoside.