222191-90-4

Upstream product

• 197716-38-4 2,3,5-tri-O-benzyl-1-O-methyl-D-xylofuranoside 
• 100-53-8 phenylmethanethiol 
• 1824-96-0 methyl xylofuranoside 
• 532-20-7 D-xylofuranose 

Downstream Products

• 222191-91-5 2,3,5-tri-O-benzyl-4-O-methanesulfonyl-D-xylose dibenzyl dithioacetal 
• 6741-71-5 1-(4-thio-L-arabino-furanosyl)thymine 

Relevant academic research and scientific papers

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.