1241784-88-2

Upstream product

• 14204-24-1 N-(phenylthio)succinimide 
• 131118-61-1 3'-tert-butyldimethylsilylthymidine 5'-carboxaldehyde 
• 931-59-9 benzenesulfenyl chloride 
• 108-98-5 thiophenol 
• 40733-27-5 3'-O-(t-butyldimethylsilyl)thymidine 

Downstream Products

• 1241784-90-6 C₂₂H₃₁⁽²⁾HN₂O₅SSi 
• 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 
• 1182869-38-0 1-[4-benzenesulfenyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-α-L-threo-pentofuranosyl]thymine 
• 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 academic research and scientific papers

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.

Self-sacrificing acetylation observed during attempted desilylation of 1-[4-benzenesulfonyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-5-O-methanesulfonyl- α-l-threo-pentofuranosyl]thymine

Desilylation of 1-[4-benzenesulfonyl-3-O-(tert-butyldimethylsilyl)-2-deoxy- 5-O-methanesulfonyl-α-l-threo-pentofuranosyl]thymine (4) with Bu 4NF/THF, when carried out at room temperature, gave four products. Among these, there were 1-[3-O-acetyl-4-benzenesulfonyl-2-deoxy-5-O- methanesulfonyl-α-l-threo-pentofuranosyl]thymine (7) and thymine. A possible reaction mechanism is proposed, which suggests the origin of 3′-O-acetyl group of 7 and thymine as well as structures of the other two products (9a and 9b).