1182869-38-0

Basic information

• Product Name: 1-[4-benzenesulfenyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-α-L-threo-pentofuranosyl]thymine
• Synonyms: 1-[4-benzenesulfenyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-α-L-threo-pentofuranosyl]thymine
• CAS NO: 1182869-38-0
• Molecular Weight: 464.658
• Mol File: 1182869-38-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-[4-benzenesulfenyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-α-L-threo-pentofuranosyl]thymine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[4-benzenesulfenyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-α-L-threo-pentofuranosyl]thymine(1182869-38-0)
• EPA Substance Registry System: 1-[4-benzenesulfenyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-α-L-threo-pentofuranosyl]thymine(1182869-38-0)

Safety Data

• Hazardous Substances Data: 1182869-38-0(Hazardous Substances Data)

Upstream product

• 40733-27-5 3'-O-(t-butyldimethylsilyl)thymidine 
• 108-98-5 thiophenol 
• 131118-61-1 3'-tert-butyldimethylsilylthymidine 5'-carboxaldehyde 
• 14204-24-1 N-(phenylthio)succinimide 
• 4551-15-9 phenylthiotrimethylsilane 
• 1241784-88-2 C₂₂H₃₀N₂O₅SSi 

Downstream Products

• 1182869-54-0 1-[4-benzenesulfenyl-3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-α-L-threo-pentofuranosyl]thymine 
• 1182869-40-4 4'-benzenesulfonyl-3',5'-bis-O-(tert-butyldimethylsilyl)thymidine 
• 1182869-57-3 C₂₈H₄₆N₂O₅SSi₂ 
• 1182869-39-1 1-[4-benzenesulfonyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-α-L-threo-pentofuranosyl]thymine 
• 1182869-58-4 1-[4-benzenesulfonyl-3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-α-L-threo-pentofuranosyl]thymine 

Relevant articles and documents

Nucleophilic substitution approach to 4′-substituted thymidines by employing 4′-benzenesulfonyl leaving group

Synthesis of 4′-substituted thymidines was investigated based on nucleophilic substitution using organosilicon and organoaluminum reagents. Two substrates having a benzenesulfonyl leaving group at the 4′-position were prepared for this purpose: 1-[4-benzenesulfonyl-3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-α-l-threo-pentofuranosyl]thymine (8α) and the 4′-(benzenesulfonyl)thymidine derivative (8β). The reaction of 8α with organosilicon reagents (Me3SiCH2CH{double bond, long}CH2 and Me3SiN3) in combination with SnCl4 gave preferentially the 4′-substituted β-d-isomer: the 4′-allyl (12β) and 4′-azido (15β) derivatives, respectively. The reaction of 8α with AlMe3, however, gave the 4′-methyl-α-l-isomer (16α) as the major product, presumably through an ion pair mechanism. By employing the substrate 8β in this reaction, the 4′-methylthymidine derivative (16β) was obtained exclusively in high yield. The 4′-ethyl (20β) and 4′-cyano (24β) derivatives were also synthesized by reacting 8β with the respective organoaluminum reagent.