Synthesis and biological activity of 2'-fluoro-2-halo derivatives of 9-. beta.-D-arabinofuranosyladenine

JA Montgomery, AT Shortnacy-Fowler…

Index: Montgomery, John A.; Shortnacy-Fowler, Anita T.; Clayton, Sarah D.; Riordan, James M.; Secrist, John A. Journal of Medicinal Chemistry, 1992 , vol. 35, # 2 p. 397 - 401

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Citation Number: 153

Abstract

The synthesis of 2-halc& (2-deoxy-2-fluoro-fl-~-arabinofuranosyl) adenines (4b and 4d) by coupling the 2, 6-dihalopurine with 3-acetyl-5-benzoyl-2-deoxy-2-fluoro-~-arabinofuranosyl bromide (2) followed by replacement of the &halogen with concomitant removal of the acyl blocking groups is described. 2-Fluoroadenine derivative 4g had to be prepared by the diazotization-fluorination of 2-aminoadenine nucleoside 40. All three nucleosides ...

 Related Synthetic Route
N/A Structure

137648-17-0

N/A

~73%

[(2S,4S,5R)-5-(6-amino-2-fluoropurin-9-yl)-4-fluorooxolan-2-yl]methanol Structure

137648-20-5

[(2S,4S,5R)-5-(...

2-fluoro-9-(5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purin-6-amine Structure

137648-18-1

2-fluoro-9-(5-O...

~%

[(2S,4S,5R)-5-(6-amino-2-fluoropurin-9-yl)-4-fluorooxolan-2-yl]methanol Structure

137648-20-5

[(2S,4S,5R)-5-(...

2-fluoro-9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purin-6-amine Structure

134217-14-4

2-fluoro-9-(3-O...

~%

[(2S,4S,5R)-5-(6-amino-2-fluoropurin-9-yl)-4-fluorooxolan-2-yl]methanol Structure

137648-20-5

[(2S,4S,5R)-5-(...

9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purine-2,6-diamine Structure

103885-02-5

9-(3-O-acetyl-5...

~%

[(2S,4S,5R)-5-(6-amino-2-fluoropurin-9-yl)-4-fluorooxolan-2-yl]methanol Structure

137648-20-5

[(2S,4S,5R)-5-(...


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