160882-24-6

Basic information

• Product Name: methyl 2,5-anhydro-3-O-benzyl-2,5-dideoxy-2-thio-β-D-arabino-pentofuranoside
• Synonyms: methyl 2,5-anhydro-3-O-benzyl-2,5-dideoxy-2-thio-β-D-arabino-pentofuranoside
• CAS NO: 160882-24-6
• Molecular Weight: 252.334
• Mol File: 160882-24-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: methyl 2,5-anhydro-3-O-benzyl-2,5-dideoxy-2-thio-β-D-arabino-pentofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,5-anhydro-3-O-benzyl-2,5-dideoxy-2-thio-β-D-arabino-pentofuranoside(160882-24-6)
• EPA Substance Registry System: methyl 2,5-anhydro-3-O-benzyl-2,5-dideoxy-2-thio-β-D-arabino-pentofuranoside(160882-24-6)

Safety Data

• Hazardous Substances Data: 160882-24-6(Hazardous Substances Data)

Upstream product

• 438576-28-4 methyl 3-O-benzyl-2,5-di-O-methanesulfonyl-D-furanoyl glucoside 
• 80229-19-2 methyl 3-O-benzyl-α-D-xylo-pentofuranoside 
• 100-39-0 benzyl bromide 
• 174833-51-3 methyl 3-O-benzyl-2,5-di-O-mesyl-α-D-xylofuranoside 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 20881-04-3 1,2:3,5-di-O-isopropylidene-D-xylofuranose 
• 167500-61-0 3-O-benzyl-5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-xylofuranose 
• 85951-12-8 1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 58-86-6 D-xylose 
• 174833-52-4 methyl 3-O-benzyl-2,5-di-O-mesyl-α-D-xylofuranoside 
• 174833-53-5 methyl 2,5-anhydro-3-O-benzyl-2,5-dideoxy-2-thio-α-D-arabino-pentofuranoside 
• 174833-50-2 methyl 3-O-benzyl-β-D-xylo-pentofuranoside 
• 34370-91-7 3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 

Downstream Products

• 160882-25-7 3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose 

Relevant articles and documents

Synthesis of iminothiasugar as a potential transition-state analog inhibitor of glycosyltransfer reactions

Iminothiasugar 1, a potential transition-state analog inhibitor of glycosidases, was synthesized in 10 steps from D-xylose.

A Novel Synthesis of 2′-Modified 2′-Deoxy-4′-thiocytidines from D-Glucose

Novel 2′-deoxycytidine antimetabolites, specifically several 2′-modified 2′-deoxy-4′-thiocytidines, were synthesized as potential new antineoplastic agents. Methyl 3-O-benzylxylofuranoside was converted to a 1,4-anhydro-4-thioarabitol 24. Protection of the primary alcohol of 24 gave a common intermediate (15) which was useful for the synthesis of various 2′-modified 2′-deoxy-4′-thionucleosides. Oxidation of the secondary hydroxyi group of 15, followed by the Wittig reaction or treatment with (diethylamido)sulfur trifluoride (DAST) produced 2-deoxy-2-methylene (26) and 2-deoxy-2,2-difluoro (34) derivatives, respectively. Unique Pummerer-type glycosylation between the corresponding sulfoxides and trimethylsilylated N4-acetylcytosine produced 2′-deoxy-2′-methylene- (10) and 2′-deoxy-2′,2′-difluoro-4′-thiocytidines (11). On the other hand, treatment of 15 with DAST introduced a fluorine atom with retention of the 2′-stereochemistry, yielding 40. In contrast, the Mitsunobu reaction of 3-O-benzoyl derivative 53 which was obtained from 15 in five steps, using diphenylphosphoryl azide gave azide derivative 54 with inverted stereochemistry. These derivatives were converted to the corresponding 1-O-acetyl derivatives via the usual Pummerer rearrangement, which were in turn used to synthesize 4′-thiocytidines 12 and 58. Among the 2′-modified 4′-thiocytidines obtained, 2′-methylene (10) and 2′-fluoro (12) derivatives were found to have potent antineoplastic properties in vitro.