152039-45-7

Basic information

• Product Name: 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-β-D-erythro-pentofuranosyl)thymine
• Synonyms: 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-β-D-erythro-pentofuranosyl)thymine
• CAS NO: 152039-45-7
• Molecular Weight: 634.825
• Mol File: 152039-45-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-β-D-erythro-pentofuranosyl)thymine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-β-D-erythro-pentofuranosyl)thymine(152039-45-7)
• EPA Substance Registry System: 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-β-D-erythro-pentofuranosyl)thymine(152039-45-7)

Safety Data

• Hazardous Substances Data: 152039-45-7(Hazardous Substances Data)

Upstream product

• 152039-44-6 methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methylbenzenesulfonyl)-D-erythro-pentofuranoside 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 

Downstream Products

• 3056-17-5 stavudin 
• 15981-92-7 2,3'-anhydrothymidine 

Relevant articles and documents

Synthesis of 2,3'-anhydro-2'-deoxyuridines and 2,3'-didehydro-2',3'-dideoxyuridines using polymer supported fluoride

Reaction of methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-α,β-D-eryt hro-pentofuranoside (2) with silylated uracils 3 using trimethylsilyl trifluoromethanesulfonate (TMS triflate) as catalyst afforded after crystallization in Et2O the corresponding β-nucleosides 4. Reaction of 4 with tetrabutylammonium fluoride (TBAF) or Amberlyst A-26 resin (F--form) in THF at room temperature or at reflux gave the corresponding deprotected 2,3'-anhydro-2'-deoxyuridines 6 and 2',3'-didehydro-2',3'-dideoxyuridines 7, respectively.