129468-48-0

Basic information

• Product Name: Methyl 2-deoxy-5-O-(4-phenylbenzoyl)-β-D-glyceropentofuranosid-3-ulose
• Synonyms: Methyl 2-deoxy-5-O-(4-phenylbenzoyl)-β-D-glyceropentofuranosid-3-ulose
• CAS NO: 129468-48-0
• Molecular Weight: 326.349
• Mol File: 129468-48-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Methyl 2-deoxy-5-O-(4-phenylbenzoyl)-β-D-glyceropentofuranosid-3-ulose(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-deoxy-5-O-(4-phenylbenzoyl)-β-D-glyceropentofuranosid-3-ulose(129468-48-0)
• EPA Substance Registry System: Methyl 2-deoxy-5-O-(4-phenylbenzoyl)-β-D-glyceropentofuranosid-3-ulose(129468-48-0)

Safety Data

• Hazardous Substances Data: 129468-48-0(Hazardous Substances Data)

Upstream product

• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 
• 14002-51-8 4-biphenyl-carboxylic acid chloride 
• 125611-95-2 methyl 2-deoxy-5-O-(4-phenylbenzoyl)-β-D-erythro-pentofuranoside 

Downstream Products

• 25526-93-6 alovudine 
• 129468-52-6 1-<2,3-Dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-α/β-D-erythro-pentofuranosy>-5-methyl-2,4(1H,3H)-pyrimidinedione 
• 129468-51-5 Methyl 2,3-dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-β-D-erythro-pentofuranoside 
• 172293-93-5 Biphenyl-4-carboxylic acid (2R,3R,5R)-3-hydroxy-3-hydroxymethyl-5-methoxy-tetrahydro-furan-2-ylmethyl ester 
• 172293-98-0 Methyl 3-C-(adenin-9-ylmethyl)-2-deoxy-5-O-(4-phenylbenzoyl)-β-D-erythro-pentofuranoside 
• 172293-99-1 Methyl 2-deoxy-5-O-(4-phenylbenzoyl)-3-C-((thymin-1-yl)methyl)-β-D-erythro-pentofuranoside 
• 172342-53-9 Biphenyl-4-carboxylic acid (2S,5R)-5-methoxy-3-methylene-tetrahydro-furan-2-ylmethyl ester 
• 129468-49-1 Methyl 2-deoxy-5-O-(4-phenylbenzoyl)-β-D-threo-pentofuranoside 

Relevant articles and documents

2-Deoxy-3-C-(hydroxymethyl)-D-pentofuranose Derivatives: Stereoselective Synthesis and Conversion into a Novel Class of Nucleoside Analogues

Oxidation of pure anomers of 5-O-monoprotected methyl 2-deoxy-D-ribofuranosides 3-6 followed by Lombardo methylenation afforded the novel 3-C-methylene pentofuranosides 11 - 14.Subsequent osmium tetraoxide-catalyzed dihydroxylations of 11, 13, and 14 afforded a mixture of erythro- and threo-configured 3-C-hydroxymethyl furanosides 15/16, 18/19, and 20/21, respectively.However, analogous dihydroxylation of 5-O-(4-phenylbenzoyl)-protected β-anomer 12 proceeded with complete stereoselectivity to give 3-C-(hydroxymethyl)-β-D-erythro pentofuranoside 17 in 76percent yield.Conversion of 17 to the corresponding primary tosylate 22, followed by base-catalyzed nucleophilic attack by the nucleobases adenine and thymine, afforded after deprotection compounds 25 and 26, respectively, as the first examples of a novel class of nucleoside analogues.