New syntheses of 2′- C-methylnucleosides starting from d-glucose and d-ribose

Effective general methods have been developed for the synthesis of 2′- C-methylnucleosides starting from d-glucose and d-ribose. 3- O-benzyl-1,2- O-isopropylidene-3- C-methyl-α- d-allofuranose was prepared in 5 steps from d-glucose and converted into 1,2,3-tri- O-acetyl-2- C-methyl-5- O- p-methylben...

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Bibliographic Details
Published in:Carbohydrate research 1987-09, Vol.166 (2), p.219-232
Main Authors: Beigelman, Leon N., Ermolinsky, Boris S., Gurskaya, Galina V., Tsapkina, Elena N., Karpeisky, Marat Ya, Mikhailov, Sergey N.
Format: Article
Language:English
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Summary:Effective general methods have been developed for the synthesis of 2′- C-methylnucleosides starting from d-glucose and d-ribose. 3- O-benzyl-1,2- O-isopropylidene-3- C-methyl-α- d-allofuranose was prepared in 5 steps from d-glucose and converted into 1,2,3-tri- O-acetyl-2- C-methyl-5- O- p-methylbenzoyl- d-ribofuranose ( 5), the starting compound for nucleoside synthesis. Compound 5 was also synthesised from 2- C-hydroxymethyl-2,3- O-isopropylidene-5- O-trityl- d-ribofuranose, prepared in 3 steps from d-ribose. Condensation of 5 with the bis-trimethylsilyl derivatives of uracil, N 4-benzoylcytosine, and N 6-benzoyladenine in the presence of F 3CSO 3OSiMe 3 followed by removal of the protecting acyl groups yielded the corresponding 2′- C-methylnucleosides.
ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(87)80059-9