213973-69-4

Upstream product

• 79-22-1 methyl chloroformate 
• 1055036-91-3 (R)-2-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-but-3-enoic acid 
• 100-51-6 benzyl alcohol 
• 77-76-9 2,2-dimethoxy-propane 
• 358673-49-1 benzyl 5-(R)-N-Cbz-5,6-dideoxy-2,3-O-isopropylidene-β-D-ribo-hept-6-enfuranoside 
• 213973-68-3 (S)-2-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-but-3-en-1-ol 
• 501-53-1 benzyl chloroformate 
• 358673-43-5 (3aR,4R,6R,6aR)-4-Benzyloxy-2,2-dimethyl-6-((E)-3-thiocyanato-propenyl)-tetrahydro-furo[3,4-d][1,3]dioxole 
• 358673-48-0 (3aR,4R,6R,6aR)-4-Benzyloxy-6-((R)-1-isothiocyanato-allyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole 

Downstream Products

• 191997-66-7 (S)-Benzyloxycarbonylamino-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetic acid methyl ester 

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.