134700-20-2

Basic information

• Product Name: α-(E)-5-(2-bromovinyl)-3',5'-di-O-p-toluoyl-2'-deoxy-4'-thiothymidine
• CAS NO: 134700-20-2
• Molecular Weight: 585.475
• Mol File: 134700-20-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: α-(E)-5-(2-bromovinyl)-3',5'-di-O-p-toluoyl-2'-deoxy-4'-thiothymidine(CAS DataBase Reference)
• NIST Chemistry Reference: α-(E)-5-(2-bromovinyl)-3',5'-di-O-p-toluoyl-2'-deoxy-4'-thiothymidine(134700-20-2)
• EPA Substance Registry System: α-(E)-5-(2-bromovinyl)-3',5'-di-O-p-toluoyl-2'-deoxy-4'-thiothymidine(134700-20-2)

Safety Data

• Hazardous Substances Data: 134700-20-2(Hazardous Substances Data)

Upstream product

• 73446-72-7 2,4-bis-O-(trimethylsilyl)-(E)-5-(2-bromovinyl)uracil 
• 134700-21-3 C₂₁H₂₁BrO₄S 
• 169736-17-8 1-O-acetyl-2-deoxy-4-thio-3,5-di-O-p-toluoyl-4-thio-D-erythro-pentofuranose 
• 69304-49-0 (E)-5-(2-bromovinyl)uracil 
• 134939-04-1 benzyl 2-deoxy-1,4-dithio-3,5-di-O-p-toluoyl-D-erythro-pentofuranoside 
• 134700-25-7 (2R,3S)-5-(benzylthio)-2-(hydroxymethyl)tetrahydrothiophen-3-ol 
• 134938-97-9 benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro-pentofuranoside 

Downstream Products

• 134699-94-8 α-(E)-5-(2-bromovinyl)-2'-deoxy-4'-thiouridine 

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.