40601-49-8

Basic information

• Product Name: 2',3'-di-O-p-tolylsulphonyladenosine
• CAS NO: 40601-49-8
• Molecular Weight: 575.623
• Mol File: 40601-49-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2',3'-di-O-p-tolylsulphonyladenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3'-di-O-p-tolylsulphonyladenosine(40601-49-8)
• EPA Substance Registry System: 2',3'-di-O-p-tolylsulphonyladenosine(40601-49-8)

Safety Data

• Hazardous Substances Data: 40601-49-8(Hazardous Substances Data)

Upstream product

• 127246-75-7 N⁶-benzoyl-2',3'-di-O-p-tolylsulphonyladenosine 
• 98-59-9 p-toluenesulfonyl chloride 
• 4546-55-8 N-benzoyladenosine 

Downstream Products

• 51600-11-4 5'-O-(p-methoxyphenyldiphenylmethyl)adenosine 
• 110142-97-7 9-<5-O-(monomethoxytrityl)-3-deoxy-β-D-threo-pentofuranosyl>adenine 
• 127277-91-2 5'-O-monomethoxytrityl-2',3'-di-O-p-tolylsulphonyladenosine 

Relevant articles and documents

REACTION OF ADENINE NUCLEOSIDES, TOSYLATED IN THE CARBOHYDRATE MOIETY, WITH LITHIUM TRIETHYLBOROHYDRIDE

The reaction of lithium triethylborohydride with the 2',3'-di-O-p-tolylsulphonyl derivatives of 9-β-D-ribofuranosyladenine, 9-β-D-arabinofuranosyladenine, 9-β-D-xylofuranosyladenine and 9-β-D-lyxofuranosyladenine was studied.The reaction of 2',3'-di-O-p-tolylsulphonyladenosine with LiEt3BH gave 9-(3-deoxy-β-D-threo-pentofuranosyl)adenine.This rearrangement reaction was used for the synthesis of 9-(3,5-dideoxy-β-D-threo-pentofuranosyl)adenine in one step from 2',3',5'-tri-O-p-tolylsulphonyladenosine in 58percent yield.The p-tolylsulphonyl group in the 2'-"up" configuration of unprotected adenine nucleosides was preferentially attacked by LiEt3BH giving S-O-bond scission.This was shown by the formation of 9-(3-deoxy-β-D-threo-pentofuranosyl)adenine from 2',3'-di-O-p-tolylsulphonyl-9-β-D-arabinofuranosyladenine and by the formation of 9-β-D-lyxofuranosyladenine from 2'-O-p-tolylsulphonyl-9-β-D-lyxofuranosyladenine with LiEt3BH. 9-β-D-Lyxofuranosyladenine was synthesized from 3',5'-di-O-benzoyl-9-β-D-xylofuranosyladenosine in 88percent yield using a triflate displacement reaction.