Use of selenium in carbohydrate chemistry: Preparation of C-glycoside congeners

3,4,5,7-Tetra- O-benzyl- d- gluco-hept-1-enitol was submitted to a selenocyclisation-oxidation-elimination sequence to provide 2,6-anhydro-3,4,5,7-tetra- O-benzyl-1-deoxy- d- gluco-hept-1-enitol in 54% yield. Treatment of methyl 2,3,4-tri- O-benzyl-α- d-glucopyranoside with N-phenylselenophthalimide...

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Bibliographic Details
Published in:Carbohydrate research 1985-01, Vol.136, p.369-374
Main Authors: Lancelin, Jean-Marc, Pougny, Jean-Rene, Sinaÿ, Pierre
Format: Article
Language:English
Subjects:
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Summary:3,4,5,7-Tetra- O-benzyl- d- gluco-hept-1-enitol was submitted to a selenocyclisation-oxidation-elimination sequence to provide 2,6-anhydro-3,4,5,7-tetra- O-benzyl-1-deoxy- d- gluco-hept-1-enitol in 54% yield. Treatment of methyl 2,3,4-tri- O-benzyl-α- d-glucopyranoside with N-phenylselenophthalimide gave methyl 2,3,4-tri- O-benzyl-6-deoxy-6-phenylseleno-α- d-glucopyranoside which was transformed to methyl 2,3,4-tri- O-benzyl-6-deoxy-α- d- xylo-hex-5-enopyranoside.
ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(85)85210-1