Journal of medicinal chemistry

Synthesis and biological evaluation of 4-purinylpyrrolidine nucleosides

ML Peterson, R Vince

Index: Peterson, Mark L.; Vince, Robert Journal of Medicinal Chemistry, 1991 , vol. 34, # 9 p. 2787 - 2797

Full Text: HTML

Citation Number: 94

Abstract

The synthesis of several novel carbocyclic purine nucleosides that incorporate a nitrogen in place of carbon 3 of the cyclopentyl moiety are described. These analogues are all derived from the key stereochemically defined intermediate N-(tert-butoxycarbonyl)-0-[(4metho~ henyl) dipheny~ ethyl]-t~~-4-hy~ ox~~ prolinol (19), which was accessible in 61.1% overall yield for a five-step sequence starting from cis-4hydroxy-~-proline. The heterocyclic bases, ...

 Related Synthetic Route
Boc-Hyp-OMe Structure

74844-91-0

Boc-Hyp-OMe

~10%

BOC-HYP-OL Structure

61478-26-0

BOC-HYP-OL

N-(tert-butoxycarbonyl)-trans-4-acetoxy-D-proline methyl ester Structure

135042-16-9

N-(tert-butoxyc...

~99%

(2R,4S)-tert-Butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate Structure

77450-03-4

(2R,4S)-tert-Bu...

Di-tert-butyl dicarbonate Structure

24424-99-5

Di-tert-butyl d...

~%

(2R,4S)-tert-Butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate Structure

77450-03-4

(2R,4S)-tert-Bu...

N-Boc-cis-4-Hydroxy-D-proline Structure

135042-12-5

N-Boc-cis-4-Hyd...

~%

(2R,4S)-tert-Butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate Structure

77450-03-4

(2R,4S)-tert-Bu...

N-Boc-cis-4-hydroxy-D-proline methyl ester Structure

114676-69-6

N-Boc-cis-4-hyd...

~%

(2R,4S)-tert-Butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate Structure

77450-03-4

(2R,4S)-tert-Bu...

cis-4-Hydroxyproline Structure

2584-71-6

cis-4-Hydroxyproline

~%

(2R,4S)-tert-Butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate Structure

77450-03-4

(2R,4S)-tert-Bu...

(2R,4S)-tert-Butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate Structure

77450-03-4

(2R,4S)-tert-Bu...

~%

[(2R,4R)-4-(2,6-diaminopurin-9-yl)pyrrolidin-2-yl]methanol Structure

135042-30-7

[(2R,4R)-4-(2,6...

N/A Structure

135042-21-6

N/A

~%

[(2R,4R)-4-(2,6-diaminopurin-9-yl)pyrrolidin-2-yl]methanol Structure

135042-30-7

[(2R,4R)-4-(2,6...

N-Boc-cis-4-Hydroxy-D-proline Structure

135042-12-5

N-Boc-cis-4-Hyd...

~%

[(2R,4R)-4-(2,6-diaminopurin-9-yl)pyrrolidin-2-yl]methanol Structure

135042-30-7

[(2R,4R)-4-(2,6...

N-Boc-cis-4-hydroxy-D-proline methyl ester Structure

114676-69-6

N-Boc-cis-4-hyd...

~%

[(2R,4R)-4-(2,6-diaminopurin-9-yl)pyrrolidin-2-yl]methanol Structure

135042-30-7

[(2R,4R)-4-(2,6...

N-(tert-butoxycarbonyl)-trans-4-acetoxy-D-proline methyl ester Structure

135042-16-9

N-(tert-butoxyc...

~%

[(2R,4R)-4-(2,6-diaminopurin-9-yl)pyrrolidin-2-yl]methanol Structure

135042-30-7

[(2R,4R)-4-(2,6...

cis-4-Hydroxyproline Structure

2584-71-6

cis-4-Hydroxyproline

~%

[(2R,4R)-4-(2,6-diaminopurin-9-yl)pyrrolidin-2-yl]methanol Structure

135042-30-7

[(2R,4R)-4-(2,6...

N/A Structure

135042-27-2

N/A

~0%

[(2R,4R)-4-(2,6-diaminopurin-9-yl)pyrrolidin-2-yl]methanol Structure

135042-30-7

[(2R,4R)-4-(2,6...


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