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Details for article 190 of 252 found articles
| Title: |
Synthesis of Furanose Glycosides of Abequose (3, 6-Dideoxy-D-Xylo-Hexose) |
| Author: |
Moradei, O. Mortier, C. du Varela, O. de Lederkremer, R. M. |
| Appeared in: |
Journal of carbohydrate chemistry |
| Paging: | Volume 10 (1991) nr. 3 pages 469-479 |
| Year: |
1991 |
| Contents: |
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 glycosylation of 9 with methanol and ethanol afforded stereoselectively methyl (10) and ethyl 2,5-di-O-benzoyl-3,6-dideoxy-β-D-xylo-hexofuranoside (11), respectively. |
| Publisher: |
Taylor & Francis |
| Source file: |
Elektronische Wetenschappelijke Tijdschriften |
Details for article 190 of 252 found articles
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