A stereoselective synthesis of 9-(3- O-benzyl-5- O-tetrahydropyranyl-β- d-arabinofuranosyl)adenine, a potentially useful intermediate for ribonucleoside synthesis

A novel synthesis for preparing 9-(3- O-benzyl-5- O-tetrahydropyranyl-β- d-arabinofuranosyl)adenine ( 6 ) has been developed which does not require sub zero temperatures or exotic reagents. A key step in this synthesis is the selective protection of the 3′-OH of ara-A with a benzyl group. The 5′-OH...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2004-04, Vol.60 (15), p.3445-3449
Main Authors: Woltermann, Christopher J., Lapin, Yuri A., Kunnen, Kevin B., Tueting, David R., Sanchez, Ignacio H.
Format: Article
Language:English
Subjects:
9-(2,3-Dideoxy-2-fluoro-β- d- threo-pentofuranosyl)adenine
9-(3- O-Benzyl-5- O-tetrahydropyranyl-β- d-arabinofuranosyl)adenine
Ara-A
FddA
Fluororibonucleoside
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A novel synthesis for preparing 9-(3- O-benzyl-5- O-tetrahydropyranyl-β- d-arabinofuranosyl)adenine ( 6 ) has been developed which does not require sub zero temperatures or exotic reagents. A key step in this synthesis is the selective protection of the 3′-OH of ara-A with a benzyl group. The 5′-OH is then selectively protected with DHP to yield 6 , a potentially useful intermediate. A synthesis of 9-(2,3-dideoxy-2-fluoro-β- d- threo-pentofuranosyl)adenine ( 1 , FddA), an anti-viral compound, is given to illustrate the utility of this new approach. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.02.033