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High-yield synthesis of 3′-amino-3′-deoxynucleosides. Conversion of adenosine to 3′-amino-3′-deoxyadenosine

✍ Scribed by Mirna C. Samano; Morris J. Robins

Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 277 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)80390-7

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✦ Synopsis

A S-O-silylated-2',3'-anhydroadenosine derivative underwent epoxide opening smoothly with dimethylboron bromide.

The N-benzyl carbamate derived from the trans bromohydrin was ring-closed with sodium hydride. Deprotection (fluoride, hydroxide, and hydrogenolysis) gave 3'-amino-3'-deoxyadenosine (6) in 66% yield from adenosine (9 steps).

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