129567-16-4

Upstream product

• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 
• 14002-51-8 4-biphenyl-carboxylic acid chloride 
• 125611-96-3 Methyl 2-Deoxy-3-O-(methylsulfonyl)-5-O-(4-phenylbenzoyl)-α-D-erythro-pentofuranoside 

Downstream Products

• 172293-89-9 Methyl 2,3-dideoxy-3-C-methylene-5-O-(4-phenylbenzoyl)-α-D-glycero-pentofuranoside 
• 129468-50-4 Methyl 2-deoxy-5-O-(4-phenylbenzoyl)-α-D-threo-pentofuranoside 

Relevant academic research and scientific papers

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.

A Short Route to 3'-Deoxy-3'-fluorothymidine

The 5-OH protected methyl glycosides 2 and 3 were epimerized to give the corresponding epimers 6 and 7 via an oxidation-reduction procedure.Reaction of 6 with diethylaminosulfur trifluoride (DAST) afforded the fluoro sugar 8, which was coupled with thymine to give 3'-deoxy-3'-fluorothymidine (12) after deprotection with saturated ammonia in methanol.