222191-91-5

Upstream product

• 197716-38-4 2,3,5-tri-O-benzyl-1-O-methyl-D-xylofuranoside 
• 1824-96-0 methyl xylofuranoside 
• 532-20-7 D-xylofuranose 
• 124-63-0 methanesulfonyl chloride 
• 222191-90-4 2,3,5-tri-O-benzyl-D-xylose dibenzyl dithioacetal 

Downstream Products

• 1198761-00-0 (1R,2R,3R,4S)-methanesulfonic acid 2,3-bis-benzyloxy-1-benzyloxymethyl-4-benzylsulfanyl-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-butyl ester 
• 1198761-01-1 (1R,2R,3R,4R)-methanesulfonic acid 2,3-bis-benzyloxy-1-benzyloxymethyl-4-benzylsulfanyl-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-butyl ester 
• 6741-71-5 1-(4-thio-L-arabino-furanosyl)thymine 
• 208755-45-7 1-(2,3,5-tri-O-benzyl-4-thio-L-arabino-furanosyl)thimine 
• 208755-44-6 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-α,β-L-arabinofuranose 

Relevant academic research and scientific papers

A stereoselective approach to nucleosides and 4′-thioanalogues from acyclic precursors

D- and L-nucleosides and analogues thereof, including the 4′-thionucleoside series, are one of the most important biological and pharmaceutically active classes of compounds. A novel approach to their synthesis from chiral acyclic thioaminal, bearing the nucleobase, is described.

Thiosugars, 2: Preparation of 2,3,5-tri-O-benzyl-4-thio-L-arabino- furanosides and the corresponding 4'-thionucleoside analogues

1-O-Acetyl-2,3,5-tri-O-benzyl-4-thio-L-arabino-furanose (9) has been prepared from D-xylose via the 1,4-dithio-L-arabino-furanoside 8. The crucial step of the reaction, i.e. the intramolecular cyclization of the open-chain dithioacetal 5, has been achieved in a yield of 90% by applying tetrabutylammonium iodide as promoter. Reaction of 9 with bis(trimethylsilyl)uracil or -thymine led to the benzyl derivatives 12 and 13 from which the deprotected 4'-thionucleoside analogues 14 and 15 have been prepared by debenzylation with boron tribromide.