Synthesis of furanose glycosides of abequose (3, 6-dideoxy-d-xtlo-hexose)
Hydrogenolysis of 2, 3, 5-tri-O-benzoyl-6-O-trityl-D-galactono-1, 4-lactone (2) gave the corresponding 3-deoxy-D-xyIo-hexono-l, 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...
Guardado en:
| Autores principales: | , , , |
|---|---|
| Formato: | JOUR |
| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_07328303_v10_n3_p469_Moradei |
| Aporte de: |
| id |
todo:paper_07328303_v10_n3_p469_Moradei |
|---|---|
| record_format |
dspace |
| spelling |
todo:paper_07328303_v10_n3_p469_Moradei2023-10-03T15:37:28Z Synthesis of furanose glycosides of abequose (3, 6-dideoxy-d-xtlo-hexose) Moradei, O. Mortier, C.D. Varela, O. Lederkremer, R.M.D. Hydrogenolysis of 2, 3, 5-tri-O-benzoyl-6-O-trityl-D-galactono-1, 4-lactone (2) gave the corresponding 3-deoxy-D-xyIo-hexono-l, 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-l, 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-a, p-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 βanomeric 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-p-D-xylo-hexofuranoside (11), respectively. © 1991, Taylor & Francis Group, LLC. All rights reserved. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_07328303_v10_n3_p469_Moradei |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| description |
Hydrogenolysis of 2, 3, 5-tri-O-benzoyl-6-O-trityl-D-galactono-1, 4-lactone (2) gave the corresponding 3-deoxy-D-xyIo-hexono-l, 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-l, 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-a, p-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 βanomeric 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-p-D-xylo-hexofuranoside (11), respectively. © 1991, Taylor & Francis Group, LLC. All rights reserved. |
| format |
JOUR |
| author |
Moradei, O. Mortier, C.D. Varela, O. Lederkremer, R.M.D. |
| spellingShingle |
Moradei, O. Mortier, C.D. Varela, O. Lederkremer, R.M.D. Synthesis of furanose glycosides of abequose (3, 6-dideoxy-d-xtlo-hexose) |
| author_facet |
Moradei, O. Mortier, C.D. Varela, O. Lederkremer, R.M.D. |
| author_sort |
Moradei, O. |
| title |
Synthesis of furanose glycosides of abequose (3, 6-dideoxy-d-xtlo-hexose) |
| title_short |
Synthesis of furanose glycosides of abequose (3, 6-dideoxy-d-xtlo-hexose) |
| title_full |
Synthesis of furanose glycosides of abequose (3, 6-dideoxy-d-xtlo-hexose) |
| title_fullStr |
Synthesis of furanose glycosides of abequose (3, 6-dideoxy-d-xtlo-hexose) |
| title_full_unstemmed |
Synthesis of furanose glycosides of abequose (3, 6-dideoxy-d-xtlo-hexose) |
| title_sort |
synthesis of furanose glycosides of abequose (3, 6-dideoxy-d-xtlo-hexose) |
| url |
http://hdl.handle.net/20.500.12110/paper_07328303_v10_n3_p469_Moradei |
| work_keys_str_mv |
AT moradeio synthesisoffuranoseglycosidesofabequose36dideoxydxtlohexose AT mortiercd synthesisoffuranoseglycosidesofabequose36dideoxydxtlohexose AT varelao synthesisoffuranoseglycosidesofabequose36dideoxydxtlohexose AT lederkremerrmd synthesisoffuranoseglycosidesofabequose36dideoxydxtlohexose |
| _version_ |
1782028769253392384 |