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Synthesis of (1R,3R,5S)-1-amino-3-(hydroxymethyl)bicyclo(3.1.0)hexane as a precursor for the synthesis of carbocyclic nucleosides

Authors :
Chang, Hae Sung
Bergmeier, Stephen C.
Frick, Jeffrey A.
Bathe, Andreas
Rapoport, Henry
Source :
Journal of Organic Chemistry. Sept 9, 1994, Vol. 59 Issue 18, p5336, 7 p.
Publication Year :
1994

Abstract

Synthesis of (1R,3R,5S)-1-amino-3-(hydroxymethyl)bicyclo(3.1. 0)hexane from (2S,3S)-2-amino-2,3-methanoadipate involves cyclization, elimination, reduction and hydrogenation. Conversion of (R)-2-((benzyloxy)ethyl)oxiranes to (2S,3S)-2-amino-2,3-methanoadipate involves the use of lactones. The bicyclo(3.1.0)hexane functions as a precursor in the synthesis of various carbocyclic nucleosides.

Details

ISSN :
00223263
Volume :
59
Issue :
18
Database :
Gale General OneFile
Journal :
Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
edsgcl.16375544