697766-92-0

Upstream product

• 592497-04-6 3,4,5-tri-O-benzyl-1,2-dideoxy-6-O-vinyl-D-xylohept-1-ene 
• 195873-64-4 3,4,5-tri-O-benzyl-1,2-dideoxy-D-xylohept-1-enitol 
• 592497-12-6 1,6-anhydro-3,4,5-tri-O-benzyl-2-deoxy-D-xylo-hept-1-enitol 

Downstream Products

• 697766-93-1 methyl 3,4,5-tri-O-benzyl-α-D-idoseptanoside 
• 697767-02-5 phenyl 3,4,5-tri-O-benzyl-1-thio-α-D-idoseptanoside 

Relevant academic research and scientific papers

Synthesis, crystal structure, and reactivity of a D-xylose based oxepine

The synthesis and X-ray crystal structure of a D-xylose-based oxepine (9) are reported. The oxepine was prepared from 2,3,4-tri-O-benzyl-D-xylose by the three-step sequence (Wittig olefination, vinyl ether formation, and ring closing metathesis) we recently reported. Epoxidation of this cyclic enol ether (9) using dimethyldioxirane (DMDO) gave 1,2-anhydro-β-D-idoseptanose (10), which was trapped by a number of nucleophiles to give α-idoseptanosides. The stereochemistry of epoxidation was assigned based on product analysis. Spectroscopic data of methyl 2,3,4,5-tetra-O-acetyl-α-D-idoseptanoside, derived from the methanolysis product 11, was compared to data of its enantiomer, the known methyl 2,3,4,5-tetra-O-acetyl-α-L-idoseptanoside.