90813-64-2

Upstream product

• 90813-62-0 9-(3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)adenine 
• 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 
• 122595-66-8 N⁶,5'-O-di(triphenylmethyl)-9-β-D-xylofuranosyladenine 
• 76-83-5 trityl chloride 

Relevant academic research and scientific papers

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.

2' AND 3'-KETONUCLEOSIDES AND THEIR ARABINO AND XYLO REDUCTION PRODUCTS CONVENIENT ACCESS VIA SELECTIVE PROTECTION AND OXIDATION OF RIBONUCLEOSIDES

A number of 2',5'- or 3',5'-diprotected ribonucleosides and 5'-protected 2'- or 3'-deoxy-β-D-erythro-pentofuranosyl nucleosides have been oxidized to the corresponding 3' or 2'-ketonucleoside derivatives using chromium trioxide/pyridine/acetic anhydride or dimethyl sulfoxide/acetic anhydride.Reduction of the carbonyl functions with sodium borohydride gave the inverted arabino, xylo, or deoxy-threo isomers as predominant products by attack at the less hindered α-face of the sugar ring.Parallel reductions using sodium borodeuteride corroborated the epimeric ratios by demonstrating that complete oxidation of the original hydroxyl groups had occured.The deuterium labeling also aided in making NMR spectral assignments.