Synthesis and antiviral activity of 3'-C-cyano-3'-deoxynucleosides

…, A Diaz-Ortiz, A Calvo-Mateo…

Index: Camarasa; Diaz-Ortiz; Calvo-Mateo; De las Heras; Balzarini; De Clercq Journal of Medicinal Chemistry, 1989 , vol. 32, # 8 p. 1732 - 1738

Full Text: HTML

Citation Number: 27

Abstract

A series of 3 '-C-cyano-3 '-deoxynucleosides have been synthesized and evaluated as antiviral agents. Reaction of 2', 5'-bis-O-(tert-butyldimethylsilyl)-~-~-erythro-pentofuranos-3'- ulosyl derivatives of uracil, 4-N-acetylcytosine, and adenine with sodium cyanide gave a mixture of epimeric cyanohydrins, which after 3'-deoxygenation yielded the corresponding 3'- C-cyano-3'-deoxy-~-~-xylo-pentofuranosyl derivatives 10. These compounds were ...

 Related Synthetic Route
Sodium cyanide Structure

143-33-9

Sodium cyanide

N/A Structure

86734-95-4

N/A

~%

(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-(2,2,3,3-tetramethylbutyl)oxolane-3-carbonitrile Structure

121055-66-1

(2S,3S,4R,5R)-5...

(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolane-3-carbonitrile Structure

121055-69-4

(2S,3R,4R,5R)-5...

~72%

(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolane-3-carbonitrile Structure

121123-91-9

(2S,3S,4R,5R)-5...

N/A Structure

86734-95-4

N/A

~%

(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolane-3-carbonitrile Structure

121123-91-9

(2S,3S,4R,5R)-5...

(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-(2,2,3,3-tetramethylbutyl)oxolane-3-carbonitrile Structure

121055-66-1

(2S,3S,4R,5R)-5...

~%

(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolane-3-carbonitrile Structure

121123-91-9

(2S,3S,4R,5R)-5...

(2S,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(2,4-dioxopyrimidin-1-yl)oxolane-3-carbonitrile Structure

121055-67-2

(2S,3R,4R,5R)-4...

~50%

(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolane-3-carbonitrile Structure

121123-90-8

(2S,3S,4R,5R)-5...

2',5'-bis-O-tert-butyldimethylsilyl-3'-ketouridine Structure

90813-54-0

2',5'-bis-O-ter...

~%

(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolane-3-carbonitrile Structure

121123-90-8

(2S,3S,4R,5R)-5...

(2S,3S,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(2,4-dioxopyrimidin-1-yl)oxolane-3-carbonitrile Structure

121055-64-9

(2S,3S,4R,5R)-4...

~%

(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolane-3-carbonitrile Structure

121123-90-8

(2S,3S,4R,5R)-5...

Sodium cyanide Structure

143-33-9

Sodium cyanide

2',5'-bis-O-tert-butyldimethylsilyl-3'-ketouridine Structure

90813-54-0

2',5'-bis-O-ter...

~%

(2S,3S,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(2,4-dioxopyrimidin-1-yl)oxolane-3-carbonitrile Structure

121055-64-9

(2S,3S,4R,5R)-4...

(2S,3S,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(2,4-dioxopyrimidin-1-yl)oxolane-3-carbonitrile Structure

121055-64-9

(2S,3S,4R,5R)-4...

~73%

(2S,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(2,4-dioxopyrimidin-1-yl)oxolane-3-carbonitrile Structure

121055-67-2

(2S,3R,4R,5R)-4...

2',5'-bis-O-tert-butyldimethylsilyl-3'-ketouridine Structure

90813-54-0

2',5'-bis-O-ter...

~%

(2S,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(2,4-dioxopyrimidin-1-yl)oxolane-3-carbonitrile Structure

121055-67-2

(2S,3R,4R,5R)-4...

(2S,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolane-3-carbonitrile Structure

121055-68-3

(2S,3R,4R,5R)-5...

~66%

(2S,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolane-3-carbonitrile Structure

121055-70-7

(2S,3S,4R,5R)-5...

4-N-acetyl-1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuranos-3'-ulosyl]cytosine Structure

121055-63-8

4-N-acetyl-1-[2...

~%

(2S,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolane-3-carbonitrile Structure

121055-70-7

(2S,3S,4R,5R)-5...

N-Acetylcytidine Structure

3768-18-1

N-Acetylcytidine

~%

(2S,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolane-3-carbonitrile Structure

121055-70-7

(2S,3S,4R,5R)-5...

N-[1-[(2R,3R,4S,5S)-3-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-cyanooxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide Structure

121055-65-0

N-[1-[(2R,3R,4S...

~%

(2S,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolane-3-carbonitrile Structure

121055-70-7

(2S,3S,4R,5R)-5...

4-N-acetyl-3'-C-cyano-3'-deoxycytidine Structure

121055-71-8

4-N-acetyl-3'-C...

~%

(2S,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolane-3-carbonitrile Structure

121055-70-7

(2S,3S,4R,5R)-5...

Sodium cyanide Structure

143-33-9

Sodium cyanide

4-N-acetyl-1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuranos-3'-ulosyl]cytosine Structure

121055-63-8

4-N-acetyl-1-[2...

~%

N-[1-[(2R,3R,4S,5S)-3-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-cyanooxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide Structure

121055-65-0

N-[1-[(2R,3R,4S...

N-[1-[(2R,3R,4S,5S)-3-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-cyanooxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide Structure

121055-65-0

N-[1-[(2R,3R,4S...

~73%

(2S,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolane-3-carbonitrile Structure

121055-68-3

(2S,3R,4R,5R)-5...

tert-Butyldimethylsilyl chloride Structure

18162-48-6

tert-Butyldimet...

~%

(2S,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolane-3-carbonitrile Structure

121055-68-3

(2S,3R,4R,5R)-5...

4-N-acetyl-1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuranos-3'-ulosyl]cytosine Structure

121055-63-8

4-N-acetyl-1-[2...

~%

(2S,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolane-3-carbonitrile Structure

121055-68-3

(2S,3R,4R,5R)-5...

N-Acetylcytidine Structure

3768-18-1

N-Acetylcytidine

~%

(2S,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolane-3-carbonitrile Structure

121055-68-3

(2S,3R,4R,5R)-5...

(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-(2,2,3,3-tetramethylbutyl)oxolane-3-carbonitrile Structure

121055-66-1

(2S,3S,4R,5R)-5...

~78%

(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolane-3-carbonitrile Structure

121055-69-4

(2S,3R,4R,5R)-5...

N/A Structure

86734-95-4

N/A

~%

(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolane-3-carbonitrile Structure

121055-69-4

(2S,3R,4R,5R)-5...


Home | MSDS/SDS Database Search | Journals | Product Classification | Biologically Active Compounds | Selling Leads | About Us | Disclaimer

Copyright © 2024 ChemSrc All Rights Reserved