172473-16-4

Basic information

• Product Name: 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-β-D-erythro-pentofuranosyl)-5-iodouracil
• Synonyms: 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-β-D-erythro-pentofuranosyl)-5-iodouracil
• CAS NO: 172473-16-4
• Molecular Weight: 746.695
• Mol File: 172473-16-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-β-D-erythro-pentofuranosyl)-5-iodouracil(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-β-D-erythro-pentofuranosyl)-5-iodouracil(172473-16-4)
• EPA Substance Registry System: 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-β-D-erythro-pentofuranosyl)-5-iodouracil(172473-16-4)

Safety Data

• Hazardous Substances Data: 172473-16-4(Hazardous Substances Data)

Upstream product

• 38953-72-9 5-iodo-2,4-bis-O-trimethylsilyluracil 
• 152039-44-6 methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methylbenzenesulfonyl)-D-erythro-pentofuranoside 

Downstream Products

• 144989-72-0 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-iodo-uracil 

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.