664966-19-2

Upstream product

• 100-39-0 benzyl bromide 
• 151426-71-0 1,2-di-O-isopropylidene-3-C-vinyl-β-D-allofuranose 

Downstream Products

• 664966-20-5 methyl 3,5,6-tri-O-benzyl-3-C-vinyl-D-allofuranoside 
• 664966-33-0 3-N-benzyloxymethyl-1-(2'-O-methylsulfonyl-3-C-(1(R),2-dihydroxyethyl)-3',5',6'-tri-O-benzyl-β-D-allofuranosyl)thymine 
• 664966-32-9 3-N-benzyloxymethyl-1-(2'-O-methylsulfonyl-3',5',6'-tri-O-benzyl-3'-C-vinyl-β-D-allofuranosyl)thymine 
• 664966-30-7 Acetic acid (2R,3R,4R,5R)-4-benzyloxy-2-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-((R)-1,2-bis-benzyloxy-ethyl)-4-vinyl-tetrahydro-furan-3-yl ester 
• 664966-34-1 (1S,2R,4R,5S,7R)-1-benzyloxy-2-(1(R),2-di(benzyloxy)ethyl)-7-hydroxymethyl-4-(3-N-(benzyloxymethyl)thymin-1-yl)-3,6-dioxabicyclo[3.2.0]heptane 
• 664966-31-8 3-N-benzyloxymethyl-1-(3',5',6'-tri-O-benzyl-3'-C-vinyl-β-D-allofuranosyl)thymine 
• 664966-29-4 1-(2'-O-acetyl-3',5',6'-tri-O-benzyl-3'-C-vinyl-β-D-allofuranosyl)thymine 
• 664966-25-0 (1S,2R,4R,5S,7R)-1-benzyloxy-7-benzoyloxymethyl-2-(1(R),2-di(benzyloxy)ethyl)-4-methoxy-3,6-dioxabicyclo[3.2.0]heptane 
• 664966-23-8 methyl 2-O-methylsulfonyl-3-C-(1(R),2-dihydroxyethyl)-3,5,6-tri-O-benzyl-β-D-allofuranoside 
• 664966-28-3 1,2-di-O-acetyl-3,5,6-tri-O-benzyl-3-C-vinyl-D-allofuranose 
• 664966-21-6 methyl 2-O-methylsulfonyl-3,5,6-tri-O-benzyl-3-C-vinyl-β-D-allofuranoside 
• 664966-24-9 (1S,2R,4R,5S,7R)-1-benzyloxy-2-(1(R),2-di(benzyloxy)ethyl)-7-hydroxymethyl-4-methoxy-3,6-dioxabicyclo[3.2.0]heptane 

Relevant academic research and scientific papers

Synthesis of hydroxymethyl branched [3.2.0]bicyclic nucleosides using a regioselective oxetane ring-formation.

Two [3.2.0]bicyclic nucleosides, 35 and 34, with one and two hydroxymethyl substituents, respectively, have been efficiently synthesized. A protected (3'-C-vinyl-beta-D-allofuranosyl)thymine derivative 28 was easily prepared from diacetone-D-glucose and the thymine moiety was protected with a BOM-group. After the introduction of a leaving group in the 2'-position, the subsequent nucleoside 31 was used as the substrate for a stereoselective dihydroxylation and a regioselective oxetane ring-formation to give after deprotection the bicyclic nucleoside 34. The surprisingly efficient formation of an oxetane was first discovered by serendipity on a corresponding methylfuranoside derivative. The allo-configured bicyclic nucleoside 34 was easily shortened to a ribo-configured analogue 35 by a diol-cleaving reaction and subsequent reduction. Both 34 and 35 are conformationally restricted in the important intermediate 04'-endo conformation.