208755-45-7

Upstream product

• 208755-44-6 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-α,β-L-arabinofuranose 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 100806-53-9 1,4-di-O-methanesulfonyl-2,3,5-tri-O-benzyl-D-xylitol 
• 100896-16-0 2,3,5-tri-O-benzyl-D-xylitol 
• 208755-43-5 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-L-arabinitol 
• 222191-91-5 2,3,5-tri-O-benzyl-4-O-methanesulfonyl-D-xylose dibenzyl dithioacetal 
• 197716-38-4 2,3,5-tri-O-benzyl-1-O-methyl-D-xylofuranoside 
• 1824-96-0 methyl xylofuranoside 
• 532-20-7 D-xylofuranose 

Downstream Products

• 6741-71-5 1-(4-thio-L-arabino-furanosyl)thymine 
• 6741-71-5 1-(4-thio-β-L-arabino-furanosyl)thymine 
• 6741-71-5 1-(4-thio-α-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.

Synthesis of L-enantiomers of 4'-thioarabinofuranosyl pyrimidine nucleosides

L-Enantiomers of 4'-thioarabinofuranosyl pyrimidine nucleosides were synthesized from D-xylose. Methyl 2,3,5-tri-O-benzyl-D-xylofuranoside 6 was converted to the corresponding xylitol 7, which was treated with MsCl and then Na2S to give 1,4-anhydro-L-4-thioarabitol 8. As previously reported, Pummerer rearrangement of 8 followed by glycosylation with a silylated thymine and N4-acetylcytosine derivative and deprotection gave the corresponding α- and β-L-4'-thioarabinofuranosyl pyrimidine nucleosides.