Synthesis of Furanose Glycosides of Abequose (3, 6-Dideoxy-D-Xylo-Hexose)
Publication type: Journal Article
Publication date: 1991-01-01
scimago Q3
wos Q2
SJR: 0.369
CiteScore: 2.1
Impact factor: 2.2
ISSN: 07328303, 15322327
Organic Chemistry
Biochemistry
Abstract
ABSTRACT Hydrogenolysis of 2,3,5-tri-O-benzoyl-6-O-trityl-D-galactono-1,4-lactone (2) gave the corresponding 3-deoxy-D-xylo-hexono-1,4-lactone derivative (3), which on treatment with HBr in acetic acid afforded 2,5-di-O-benzoyl-6-bromo-3,6-dideoxy-D-xylo-hexono 1,4-lactone (4). Hydrogenation of 4 led to 3,6-dideoxy-D-xylo-hexono-1,4-lactone dibenzoate (6). The overall yield of 6 from D-galactono-1, 4-lactone (1) was about 59%. Alternatively, compound 6 was prepared (67% overall yield from 1) by hydrogenolysis of 6-bromo-6-deoxy-D-galactono-1,4-lactone tribenzoate (5), obtained by treatment of 2 with HBr in dry dichloromethane. Diisoamylborane reduction of 6 gave an anomeric mixture of 2,5-di-O-benzoyl-3,6-dideoxy-α, β-D-xylo-hexofuranose (7), which on O-debenzoylation afforded 3,6-dideoxy-D-xylo-hexose (abequose, 8) whose tautomeric equilibrium was studied by 13C NMR spectroscopy. Acetylation of 7 gave the 1-O-acetyl derivative (9) mainly in the β anomeric configuration. Tin (IV) chloride promoted glycosy...
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Moradei O. et al. Synthesis of Furanose Glycosides of Abequose (3, 6-Dideoxy-D-Xylo-Hexose) // Journal of Carbohydrate Chemistry. 1991. Vol. 10. No. 3. pp. 469-479.
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Moradei O., Du Mortier C., Varela O., de Lederkremer R. M. Synthesis of Furanose Glycosides of Abequose (3, 6-Dideoxy-D-Xylo-Hexose) // Journal of Carbohydrate Chemistry. 1991. Vol. 10. No. 3. pp. 469-479.
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RIS
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TY - JOUR
DO - 10.1080/07328309108543922
UR - https://doi.org/10.1080/07328309108543922
TI - Synthesis of Furanose Glycosides of Abequose (3, 6-Dideoxy-D-Xylo-Hexose)
T2 - Journal of Carbohydrate Chemistry
AU - Moradei, O.
AU - Du Mortier, C
AU - Varela, Oscar
AU - de Lederkremer, R M
PY - 1991
DA - 1991/01/01
PB - Taylor & Francis
SP - 469-479
IS - 3
VL - 10
SN - 0732-8303
SN - 1532-2327
ER -
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BibTex (up to 50 authors)
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@article{1991_Moradei,
author = {O. Moradei and C Du Mortier and Oscar Varela and R M de Lederkremer},
title = {Synthesis of Furanose Glycosides of Abequose (3, 6-Dideoxy-D-Xylo-Hexose)},
journal = {Journal of Carbohydrate Chemistry},
year = {1991},
volume = {10},
publisher = {Taylor & Francis},
month = {jan},
url = {https://doi.org/10.1080/07328309108543922},
number = {3},
pages = {469--479},
doi = {10.1080/07328309108543922}
}
Cite this
MLA
Copy
Moradei, O., et al. “Synthesis of Furanose Glycosides of Abequose (3, 6-Dideoxy-D-Xylo-Hexose).” Journal of Carbohydrate Chemistry, vol. 10, no. 3, Jan. 1991, pp. 469-479. https://doi.org/10.1080/07328309108543922.