208755-44-6

Basic information

• Product Name: 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-α,β-L-arabinofuranose
• Synonyms: 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-α,β-L-arabinofuranose
• CAS NO: 208755-44-6
• Molecular Weight: 478.609
• Mol File: 208755-44-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-α,β-L-arabinofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-α,β-L-arabinofuranose(208755-44-6)
• EPA Substance Registry System: 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-α,β-L-arabinofuranose(208755-44-6)

Safety Data

• Hazardous Substances Data: 208755-44-6(Hazardous Substances Data)

Upstream product

• 532-20-7 L-arabinose 
• 495387-53-6 2,3,5-tri-O-benzyl-1,4-di-O-methanesulfonyl-L-arabinitol 
• 96192-07-3 2,3,5-tri-O-benzyl-L-arabinofuranose 
• 131615-65-1 methyl 2,3,5-tri-O-benzyl-α,β-L-arabinofuranoside 
• 13039-64-0 (2S,3R,4R)-2-(hydroxymethyl)-5-methoxytetrahydrofuran-3,4-diol 
• 208755-43-5 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-L-arabinitol 
• 100806-53-9 1,4-di-O-methanesulfonyl-2,3,5-tri-O-benzyl-D-xylitol 
• 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 
• 1600-27-7 mercury(II) diacetate 
• 108-24-7 acetic anhydride 
• 100896-16-0 2,3,5-tri-O-benzyl-D-xylitol 

Downstream Products

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

Relevant articles and documents

Synthesis, Reactivity, and Stereoselectivity of 4-Thiofuranosides

Thiosugars, sugars that have their endocyclic oxygen substituted for a sulfur atom, have been used as stable bioisosteres of naturally occurring glycans because the thiosugar glycosydic linkage is supposed to be stabilized toward chemical and enzymatic hydrolysis. We have performed an in-depth investigation into the stability and reactivity of furanosyl thiacarbenium ions, by assessing all four diastereoisomeric thiofuranosides experimentally and computationally. We show that all furanosyl thiacarbenium ions react in a 1,2-cis-selective manner with triethylsilane, reminiscent of their oxo counterparts. The computed conformational space occupied by the thiacarbenium ions is strikingly similar to that of the corresponding furanosyl oxycarbenium ions, indicating that the stereoelectronic substituent effects governing the stability of furanosyl oxocarbenium ions and thiacarbenium ions are very similar. While the thio-ribo-furanose appears to be less reactive than its oxo counterpart, the thio-ara-, lyxo-, and xylo-furanosides appear to be more reactive than their oxygen equivalents. These differences are accounted for using the conformational preference of the donors and the carbocation intermediates. The lower reactivity of the thio-ribo furanosides in (Lewis) acid-mediated reactions and the similarity of the thia- and oxocarbenium ions make thio-ribo-furanosides excellent stabilized analogues of the naturally occurring ribo-furanose sugars.

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.