198775-36-9

Upstream product

• 77890-04-1 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-ribo-hexitol 
• 4330-20-5 N-3-benzoylthymine 
• 37699-02-8 (3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde 
• 198775-13-2 ((3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-methanol 
• 75499-82-0 2,5-anhydro-4,5-di-O-benzoyl-1,3-O-isopropylidene-D-glucitol 
• 75499-83-1 2,5-anhydro-4,5-di-O-benzoyl-D-glucitol 
• 98-88-4 benzoyl chloride 
• 65729-81-9 2,5-anhydro-1,3-O-isopropylidene-D-glucitol 

Relevant academic research and scientific papers

Synthesis of homo-C-D4T and homo-C-thymidine

β-C-Vinyl glycoside of D-arabinofuranose was converted to the β-C- hydroxymethyl glycoside 12 which was condensed with N-3-benzoyl thymine under Mitsunobu conditions to furnish homo-C-analog 14 of the 2',3'-dideoxy-2',3'- didehydrothymidine (D4T). Synthesis of the homo-C-thymidine 18 was accomplished by the same procedure from compound 15.

D-arbinose-based synthesis of homo-C-d4T and homo-C-thymidine

2,3,5-Tri-O-benzyl-D-arabinofuranosyl halides (chloride, bromide) were reacted with AllMgBr, MeMgBr, and VinMgBr to furnish anomeric mixtures of the C-glycosyl products. The factors that influenced the β/α ratio are discussed. The α,β-C-vinyl derivative was transformed into 1-deoxy-1-C-hydroxymethyl-β and α-D-arabinofuranoses (2,5-anhydro-D-glucitol and -mannitol, respectively), separable after isopropylidenation step. 2,5-Anhydro-1,3-O-isopropylidene-D-glucitol was converted into 2,5-anhydro-6-O-triphenylmethyl-D-erythro-hex-3,4-enitol and 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-ribo-hexitol, which were coupled with N-3-benzoylthymine under the Mitsunobu conditions to furnish two analogs of nucleosides with a -CH2- insert between sugar moieties and thymine. (Chemical Equation Presented).