137719-36-9

Basic information

• Product Name: 4-amino-1-[(2R,5S)-5-(hydroxymethyl)tetrahydrothiophen-2-yl]pyrimidin-2(1H)-one
• CAS NO: 137719-36-9
• Molecular Formula: C₉H₁₃N₃O₂S
• Molecular Weight: 227.2834
• Mol File: 137719-36-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 444.5°C at 760 mmHg
• Flash Point: 222.7°C
• Density: 1.6g/cm³
• Vapor Pressure: 9.03E-10mmHg at 25°C
• Refractive Index: 1.742
• CAS DataBase Reference: 4-amino-1-[(2R,5S)-5-(hydroxymethyl)tetrahydrothiophen-2-yl]pyrimidin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-amino-1-[(2R,5S)-5-(hydroxymethyl)tetrahydrothiophen-2-yl]pyrimidin-2(1H)-one(137719-36-9)
• EPA Substance Registry System: 4-amino-1-[(2R,5S)-5-(hydroxymethyl)tetrahydrothiophen-2-yl]pyrimidin-2(1H)-one(137719-36-9)

Safety Data

• Hazardous Substances Data: 137719-36-9(Hazardous Substances Data)

Upstream product

• 137719-21-2 4(S)-(acetylthio)-5-<(tert-butyldiphenylsilyl)oxy>pentanoic acid methyl ester 
• 137719-23-4 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thioribofuranose 
• 185303-83-7 (S)-5-Hydroxymethyl-tetrahydro-thiophen-2-ol 
• 185303-82-6 (S)-5-Oxo-tetrahydro-thiophene-2-carbaldehyde 
• 185303-85-9 Acetic acid (S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-thiophen-2-yl ester 
• 137819-77-3 1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-β-D-ribofuranosyl>cytosine 

Relevant articles and documents

Expeditious syntheses of sugar-modified nucleosides and collections thereof exploiting furan-, pyrrole-, and thiophene-based siloxy dienes

A series of individual sugar-modified pyrimidine nucleosides including enantiomerically enriched 2',3'-dideoxynucleosides 14a-c (α and β anomers of L- and D-series), 2',3'-dideoxy-4'-thionucleosides 21a-c (α and β anomers of L- and D-series), and 2',3'-dideoxy-4'-azanucleosides 28a-c (β anomers of L- and D-series) were synthesized, with uniform chemistry and high stereochemical efficiency, exploiting a triad of versatile heterocyclic siloxy dienes, namely, 2-(tert-butyldimethylsiloxy)furan (TBSOF), 2-(tert- butyldimethylsiloxy)thiophene (TBSOT), and N-(tert-butoxycarbonyl)-2-(tert- butyldimethylsiloxy)pyrrole (TBSOP). The synthetic procedure advantageously used both enantiomers of glyceraldehyde acetonide (D-1 and L-1) as sources of chirality and as synthetic equivalents of the formyl cation. The outlined chemistry also allowed for the rapid assemblage of a 30-member collection of racemic nucleosides (D,L-L) as well as one 15-member ensemble of chiral analogues (L-L), along with some related sublibraries.

2',3'-dideoxy-4'-thioribonucleosides and synthetic precursors thereof

2',3'-dideoxy-4'-thioribonucleosides useful as antiviral agents in the treatment and prevention of AIDS are disclosed. In accordance with one aspect of the invention there are provided compounds of the formula STR1 where X=H, N3 or F, and B is a member selected from the group consisting of pyrimidine, 5-azapyrimidine, 6-azapyrimidine, 3-deazapyrimidine, purine, 3-deazapurine, 7-deazapurine, 8-azapurine, and 2-azapurine bases. The intermediate 1-O-acetyl-5-O-t-butyldiphenylsilyl-4-thio-2,3-dideoxyribofuranose is useful in the production of certain of the 2',3'-dideoxy-4'-thioribonucleosides. Other intermediates include the 4-thio-2,3-dideoxyribofuranose having different hydroxyl protecting groups and leaving groups.

2',3'-dideoxy-4'-thioribonucleosides as antiviral agents

2'3'-dideoxy-4'-thioribonucleosides useful as antiviral agents in the treatment and prevention of AIDS are disclosed. In accordance with one aspect of the invention there are provided compounds of the formula STR1 where X=H, N3 or F, and B is a member selected from the group consisting of pyrimidine, 5-azapyrimidine, 6-azapyrimidine, 3-deazapyrimidine, purine, 3-deazapurine, 7-deazapurine, 8-azapurine, and 2-azapurine bases. The intermediate 1-O-acetyl-5-O-t-butyldiphenylsilyl-4-thio-2,3-dideoxyribofuranose useful in the production of certain of the 2',3'-dideoxy-4'-thioribonucleosides is also disclosed.