152711-06-3

Upstream product

• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 152711-01-8 Methyl 2,5-di-O-benzoyl-3-deoxy-3-fluoro-β-D-arabinofuranoside 
• 152711-04-1 C₁₉H₁₆BrFO₅ 
• 152711-02-9 C₁₉H₁₆BrFO₅ 
• 152711-00-7 Methyl 3-deoxy-3-fluoro-β-D-arabinofuranoside 
• 126716-27-6 methyl 2,5-di-O-benzoyl-3-fluoro-3-deoxy-α-D-ribofuranoside 
• 112695-36-0 methyl 2,5-di-O-benzoyl-3-fluoro-3-deoxy-β-D-ribofuranoside 
• 28867-47-2 methyl 5-O-benzyl-3-fluoro-3-deoxy-β-D-arabino-furanoside 
• 14537-06-5 Methyl 2,5-di-O-benzoyl-3-deoxy-3-fluoro-α-D-arabinofuranoside 
• 14980-09-7 methyl 5-O-benzyl-3-fluoro-3-deoxy-α-D-arabino-furanoside 
• 14645-35-3 methyl 3-fluoro-α-D-3-deoxy-arabinofuranoside 
• 152785-09-6 1,5-Di-O-benzoyl-2,3-dideoxy-3-fluoro-β-D-erythro-pentofuranose 
• 152785-10-9 1,5-Di-O-benzoyl-2,3-dideoxy-3-fluoro-α-D-erythro-pentofuranose 

Downstream Products

• 25526-93-6 alovudine 

Relevant academic research and scientific papers

A facile synthesis of 3'-deoxy-3'-fluorothymidine via a highly stereoselective glycosylation with 2,3-dideoxy-3-fluoro-D-erythro- pentofuranosyl diethyl phosphite

Coupling of 2,3-dideoxy-3-fluoro-D-erythro-pentofuranosyl diethyl phosphite with 2,4-bis(trimethylsilyl)thymine under the influence of trimethylsilyl trifluoromethanesulfonate (TM-SOTf) provides a facile and highly stereoselective entry to 3'-deoxy-3'-fluorothymidine (FLT), wherein the use of propionitrile as a solvent as well as the α-configuration of the fluorine atom at C3 has been proven to be responsible for the high β- selectivity of up to 91:9.

Synthesis of 2',3'-dideoxy-3'-fluorothymidine using individual anomers of 1,5-di-O-benzoyl-2,3-dideoxy-3-fluoro-D-erythro-pentofuranose as glycosylating agents

A convenient preparation of α- and β-anomers of 1,5-di-O-benzoyl-2,3-dideoxy-3-fluoro-D-erythro-pentofuranose is described. Each anomer is studied as the glycosylating agent in the reaction with bis-trimethylsilylated thymine in the presence of trimethylsilyl triflate. Under optimum conditions, 2',3'-dideoxy-3'-fluorothymidine (FLT) and its α-anomer are isolated in 64 and 25% yields, respectively.