172293-93-5

Basic information

• Product Name: Biphenyl-4-carboxylic acid (2R,3R,5R)-3-hydroxy-3-hydroxymethyl-5-methoxy-tetrahydro-furan-2-ylmethyl ester
• Synonyms: Biphenyl-4-carboxylic acid (2R,3R,5R)-3-hydroxy-3-hydroxymethyl-5-methoxy-tetrahydro-furan-2-ylmethyl ester
• CAS NO: 172293-93-5
• Molecular Weight: 358.391
• Mol File: 172293-93-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Biphenyl-4-carboxylic acid (2R,3R,5R)-3-hydroxy-3-hydroxymethyl-5-methoxy-tetrahydro-furan-2-ylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Biphenyl-4-carboxylic acid (2R,3R,5R)-3-hydroxy-3-hydroxymethyl-5-methoxy-tetrahydro-furan-2-ylmethyl ester(172293-93-5)
• EPA Substance Registry System: Biphenyl-4-carboxylic acid (2R,3R,5R)-3-hydroxy-3-hydroxymethyl-5-methoxy-tetrahydro-furan-2-ylmethyl ester(172293-93-5)

Safety Data

• Hazardous Substances Data: 172293-93-5(Hazardous Substances Data)

Upstream product

• 172342-53-9 Biphenyl-4-carboxylic acid (2S,5R)-5-methoxy-3-methylene-tetrahydro-furan-2-ylmethyl ester 
• 125611-95-2 methyl 2-deoxy-5-O-(4-phenylbenzoyl)-β-D-erythro-pentofuranoside 
• 129468-48-0 Methyl 2-deoxy-5-O-(4-phenylbenzoyl)-β-D-glyceropentofuranosid-3-ulose 
• 14002-51-8 4-biphenyl-carboxylic acid chloride 
• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 

Downstream Products

• 199177-93-0 Biphenyl-4-carboxylic acid (2R,3R,5R)-3-acetoxy-3-acetoxymethyl-5-methoxy-tetrahydro-furan-2-ylmethyl ester 
• 206650-01-3 Biphenyl-4-carboxylic acid (2R,3R)-3-acetoxy-3-acetoxymethyl-5-(4-isobutyrylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 206650-02-4 Biphenyl-4-carboxylic acid (2R,3R)-3-acetoxy-3-acetoxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 199177-92-9 Biphenyl-4-carboxylic acid (2R,3R,5R)-3-acetoxy-3-(tert-butyl-dimethyl-silanyloxymethyl)-5-methoxy-tetrahydro-furan-2-ylmethyl ester 
• 199177-91-8 Biphenyl-4-carboxylic acid (2R,3R,5R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester 
• 172293-99-1 Methyl 2-deoxy-5-O-(4-phenylbenzoyl)-3-C-((thymin-1-yl)methyl)-β-D-erythro-pentofuranoside 
• 172293-98-0 Methyl 3-C-(adenin-9-ylmethyl)-2-deoxy-5-O-(4-phenylbenzoyl)-β-D-erythro-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.