134699-93-7

Basic information

• Product Name: 5-(2-bromovinyl)-2'-deoxy-4'-thiouridine
• Synonyms: 5-(2-bromovinyl)-2'-deoxy-4'-thiouridine;Aids104064;Aids-104064
• CAS NO: 134699-93-7
• Molecular Formula: C11H13 Br N2 O4 S
• Molecular Weight: 349.2
• Mol File: 134699-93-7.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.859g/cm³
• CAS DataBase Reference: 5-(2-bromovinyl)-2'-deoxy-4'-thiouridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2-bromovinyl)-2'-deoxy-4'-thiouridine(134699-93-7)
• EPA Substance Registry System: 5-(2-bromovinyl)-2'-deoxy-4'-thiouridine(134699-93-7)

Safety Data

• Hazardous Substances Data: 134699-93-7(Hazardous Substances Data)

Upstream product

• 134939-01-8 (E)-5-(2-bromovinyl)-3',5'-di-O-benzyl-2'-deoxy-4'-thiothymidine 
• 134938-97-9 benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro-pentofuranoside 
• 134967-13-8 (2R,3S)-3-Benzyloxy-2-benzyloxymethyl-5-bromo-tetrahydro-thiophene 
• 134939-04-1 benzyl 2-deoxy-1,4-dithio-3,5-di-O-p-toluoyl-D-erythro-pentofuranoside 
• 134700-21-3 C₂₁H₂₁BrO₄S 
• 134700-25-7 (2R,3S)-5-(benzylthio)-2-(hydroxymethyl)tetrahydrothiophen-3-ol 
• 69304-49-0 (E)-5-(2-bromovinyl)uracil 
• 169736-17-8 1-O-acetyl-2-deoxy-4-thio-3,5-di-O-p-toluoyl-4-thio-D-erythro-pentofuranose 
• 134700-19-9 (E)-5-(2-bromovinyl)-3',5'-di-O-p-toluoyl-2'-deoxy-4'-thiothymidine 

Relevant articles and documents

Efficient syntheses of (E)-5-(2-Bromovinyl)-2'-deoxy-4'thiouridine; a nucleoside analogue with potent biological activity

(E)-5-(2-Bromovinyl)-2'-deoxy-4'-thiouridine (S-BVDU) is a potent antiherpesvirus agent and its use in gene therapy as an anticancer agent has recently been described. We here outline 2 efficient methods for the synthesis of S-BVDU. The decision as to which method is to be used depends upon the starting materials available but starting from BVU, an overall yield of β-nucleoside of 35% can be expected. From 5-ethyl-2'deoxy-4'- thiouridine, radical bromination using bromine will give a quantitative conversion to S-BVDU if unreacted starting material is recycled (50%) or using N-bromosuccinimide, a one step yield in excess of 80% can be obtained.

Antiviral pyrimidine nucleosides

Pyrimidine 4'-thionucleosides of the formula I STR1 wherein Y is hydroxy or amino, and X is chloro, bromo, iodo, trifluoromethyl, C2-6 alkyl, C2-6 alkenyl, C2-6 haloalkenyl or C2-6 alkynyl and physiologically functional derivatives thereof. These compounds have utility as anti-vital agents.

The synthesis and antiviral activity of some 4'-thio-2'-deoxy nucleoside analogues

Starting from benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro-pentofuranoside (4), the following 2'-deoxy nucleoside analogues have been synthesized: 4'-thiothymidine (8), 3'-azido-4'-thio-deoxythymidine (10), and (E)-5-(2-bromovinyl)-4'-thio-2'-deoxy