90813-64-2

Basic information

• Product Name: 9-(3-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)adenine
• Synonyms: 9-(3-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)adenine
• CAS NO: 90813-64-2
• Molecular Weight: 493.565
• Mol File: 90813-64-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 9-(3-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)adenine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-(3-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)adenine(90813-64-2)
• EPA Substance Registry System: 9-(3-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)adenine(90813-64-2)

Safety Data

• Hazardous Substances Data: 90813-64-2(Hazardous Substances Data)

Upstream product

• 122595-66-8 N⁶,5'-O-di(triphenylmethyl)-9-β-D-xylofuranosyladenine 
• 90813-62-0 9-(3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)adenine 
• 76-83-5 trityl chloride 
• 73-03-0 cordycepin 
• 127398-63-4 5'-O-trityl-2',3'-di-O-p-tolylsulphonyl-9-β-D-xylofuranosyladenine 
• 90813-63-1 9-(3-deoxy-5-O-trityl-β-D-glycero-pentofuran-2-ulosyl)adenine 

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.