358673-55-9

Upstream product

• 507-09-5 tiolacetic acid 
• 358673-53-7 tert-Butyl-[(3aR,5R,6S,6aR)-5-((R)-1-isothiocyanato-allyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-diphenyl-silane 
• 358673-51-5 tert-Butyl-[(3aR,5R,6S,6aR)-2,2-dimethyl-5-((E)-3-thiocyanato-propenyl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-diphenyl-silane 

Relevant academic research and scientific papers

Stereoselective synthesis of the 5′-aminofuranoside part of polyoxins via (3,3)-sigmatropic rearrangement of allylic thiocyanates

A new and stereoselective route for the synthesis of the benzyl 5-(R)-N-Cbz-5,6-dideoxy-2,3-O-isopropylidene-β-D-ribo-hept-6- enfuranoside 5e and 5-(R)-N-acetyl-5,6-dideoxy-1,3-O-isopropylidene-β-D-ribo-hept-6- enfuranoside 12 as useful protected precursors of the 5′-aminofuranoside part of polyoxins is presented. The key-step involves diastereoselective introduction of the amino group at C-5 of the ribose and xylose by (3,3)-sigmatropic rearrangements of the corresponding allylic thiocyanates.