137819-79-5

Usage

Molecular structure

The compound has a complex molecular structure consisting of a pyrimidine ring and a tetrahydrothiophen ring.

Stereochemistry

The compound has a (2R,5S) stereochemistry at the tetrahydrothiophen ring.

Functional groups

The compound contains a hydroxymethyl group attached to the tetrahydrothiophen ring and a methyl group attached to the pyrimidine ring.

Potential applications

The compound may have potential pharmaceutical or biological applications due to the presence of the pyrimidine ring and the tetrahydrothiophen ring.

Biological activities

Pyrimidine derivatives are known to have a variety of biological activities, including antiviral and anticancer properties.

Unique chemical properties

The presence of the tetrahydrothiophen ring and the hydroxymethyl group may give the compound unique chemical properties that could be of interest in drug development or other industrial applications.

Molecular weight

The molecular weight of the compound is approximately 254.3 g/mol.

Solubility

The compound's solubility properties are not specified in the provided material, but it may be influenced by the presence of the hydroxymethyl and methyl groups.

Stability

The stability of the compound is not specified in the provided material, but it may be affected by the presence of the pyrimidine and tetrahydrothiophen rings.

Upstream product

• 185303-85-9 Acetic acid (S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-thiophen-2-yl ester 
• 185303-83-7 (S)-5-Hydroxymethyl-tetrahydro-thiophen-2-ol 
• 185303-82-6 (S)-5-Oxo-tetrahydro-thiophene-2-carbaldehyde 
• 137719-37-0 1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-α,β-D-ribofuranosyl>thymine 
• 65-71-4 2,4-dihydroxy-5-methylpyrimidine 

Relevant academic research and scientific papers

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.

Synthesis and Anti-HIV Activity of 4'-Thio-2',3'-dideoxynucleosides

A series of 2',3'-dideoxy-4'-thionucleoside analogues of purines and pyrimidines, including 4'-thioddI (17), 4'-thioddC (27), and 4'-thioAZT (34), were synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV).A st

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.