Epimerization during the acetolysis of 3- O-acetyl-5- O-benzoyl-1,2- O-isopropylidene-3- C-methyl-α- d-ribofuranose. Synthesis of 3′- C-methylnucleosides with the β- d- ribo- and α- d- arabino configurations

Acetolysis of 3- O-acetyl-5- O-benzoyl-1,2- O-isopropylidene-3- C-methyl-α- d-ribofuranose with a high concentration of acetic acid yielded 1,2,3-tri- O-acetyl-5- O-benzoyl-3- C-methyl- d-arabinofuranose, which was used for the preparation of 3- C-methyl-α- d-arabinofuranosyl nucleosides. 3′- C-Meth...

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Bibliographic Details
Published in:Carbohydrate research 1988-10, Vol.181, p.77-88
Main Authors: Beigelman, Leon N., Gurskaya, Galina V., Tsapkina, Elena N., Mikhailov, Sergey N.
Format: Article
Language:English
Subjects:
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Nucleosides, nucleotides and oligonucleotides
Organic chemistry
Preparations and properties
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Summary:Acetolysis of 3- O-acetyl-5- O-benzoyl-1,2- O-isopropylidene-3- C-methyl-α- d-ribofuranose with a high concentration of acetic acid yielded 1,2,3-tri- O-acetyl-5- O-benzoyl-3- C-methyl- d-arabinofuranose, which was used for the preparation of 3- C-methyl-α- d-arabinofuranosyl nucleosides. 3′- C-Methylribonucleosides were also synthesized starting from 1,2,3-tri- O-acetyl-5- O-benzoyl-3- C-methyl- d-ribofuranose.
ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(88)84024-2