134700-25-7

Basic information

• Product Name: (2R,3S)-5-(benzylthio)-2-(hydroxymethyl)tetrahydrothiophen-3-ol
• Synonyms: (2R,3S)-5-(benzylthio)-2-(hydroxymethyl)tetrahydrothiophen-3-ol
• CAS NO: 134700-25-7
• Molecular Weight: 256.39
• Mol File: 134700-25-7.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (2R,3S)-5-(benzylthio)-2-(hydroxymethyl)tetrahydrothiophen-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-5-(benzylthio)-2-(hydroxymethyl)tetrahydrothiophen-3-ol(134700-25-7)
• EPA Substance Registry System: (2R,3S)-5-(benzylthio)-2-(hydroxymethyl)tetrahydrothiophen-3-ol(134700-25-7)

Safety Data

• Hazardous Substances Data: 134700-25-7(Hazardous Substances Data)

Upstream product

• 134938-97-9 benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro-pentofuranoside 

Downstream Products

• 134939-04-1 benzyl 2-deoxy-1,4-dithio-3,5-di-O-p-toluoyl-D-erythro-pentofuranoside 
• 134700-20-2 α-(E)-5-(2-bromovinyl)-3',5'-di-O-p-toluoyl-2'-deoxy-4'-thiothymidine 
• 134700-19-9 (E)-5-(2-bromovinyl)-3',5'-di-O-p-toluoyl-2'-deoxy-4'-thiothymidine 
• 134700-21-3 C₂₁H₂₁BrO₄S 
• 134699-93-7 (E)-5-(2-bromovinyl)-2'-deoxy-4'-thiouridine 
• 134699-94-8 α-(E)-5-(2-bromovinyl)-2'-deoxy-4'-thiouridine 
• 135123-45-4 C₂₇H₂₇ClN₂O₆S 

Relevant articles and documents

Acyl carbamate directing groups in nucleoside synthesis: Applications in the synthesis of 2′-deoxy-5-ethyl-4′-thiouridine

The use of the 3-O-(N-acyl)carbamoyl directing groups in the synthesis of the potent anti-Herpes virus agent 2′-deoxy-5-ethyl-4′-thio-D-uridine is described. This includes details of experiments to optimise the carbamate substitution and a multi-gram exemplification of the key steps.

STEREOSELECTIVE SYNTHESIS AND PROCESS FOR THE MANUFACTURING OF 2'-DEOXYNUCLEOSIDES

Methods for stereoselective synthesis and manufacturing of 2'-deoxynucleosides, such as 2'-ribonucleosides, are disclosed. In some embodiments, the 2'-deoxynucleoside is a β-anomer of 2'-deoxynucleoside having a 3' a hydroxyl, 4' β hydroxymethyl configuration. Nonlimiting examples of compounds prepared by the disclosed methods include 4'-thio-2'-deoxycytidine (T-dCyd) and 5-aza-4'-thio-2'-deoxycytidine (5-aza-T-dCyd; aza-T-dCyd; aza-T-dC).

Electrophilic addition to 4-thio furanoid glycal: A highly stereoselective entry to 2'-deoxy-44'-thio pyrimidine nucleosides

4-Thio furanoid glycals with different types of O-silyl protection have been prepared from benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro- pentofuranoside. Face-selectivity for PhSeCl- or N-iodosuccimide-initiated addition of a pyrimidine base to the thioglycal protected with a 3,5-O-di-r- butylsilyl group, a highly stereoselective synthesis of β-2'-deoxy-4'-thio pyrimidine nucleoside has been accomplished.