195315-76-5

Upstream product

• 1003-03-8 Cyclopentamine 
• 195315-75-4 (R)-1-((3aR,5S,6S,6aR)-6-Isothiocyanato-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol 
• 195315-72-1 Methanesulfonic acid 2-[(3aR,5S,6aR)-5-[(R)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-(6E)-ylidene]-ethyl ester 
• 195315-70-9 [(3aR,5S,6aR)-5-[(R)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-(6E)-ylidene]-acetic acid methyl ester 
• 195315-74-3 5,6-bis(O-tert-butyldimethylsilyl)-3-deoxy-1,2-O-isopropylidene-3-isothiocyanato-3-C-vinyl-α-D-glucofuranose 
• 195315-73-2 (3aR,5S,6aR)-5-[(R)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-6-[2-thiocyanato-eth-(E)-ylidene]-tetrahydro-furo[2,3-d][1,3]dioxole 
• 195315-71-0 2-[(3aR,5S,6aR)-5-[(R)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-(6E)-ylidene]-ethanol 
• 195315-69-6 [(3aR,5S,6aR)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-(6E)-ylidene]-acetic acid methyl ester 
• 103516-13-8 2-[(3aR,5S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-(6E)-ylidene]-ethanol 
• 103516-12-7 (Z)-3-deoxy-3-C-[(hydroxymethyl)methylene]-1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranose 
• 911122-63-9 3-deoxy-3-(N-cyclopentylthiocarboxamido)-1,2:5,6-di-O-isopropylidene-3-C-vinyl-α-D-glucofuranose 
• 195315-77-6 5,6-bis(O-tert-butyldimethylsilyl)-3-(N-cyclopentylthiocarboxamido)-3-deoxy-1,2-O-isopropylidene-3-C-vinyl-α-D-glucofuranose 
• 195315-65-2 Methanesulfonic acid 2-[(3aR,5S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-(6E)-ylidene]-ethyl ester 
• 195315-62-9 Methanesulfonic acid 2-[(3aR,5S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-(6Z)-ylidene]-ethyl ester 

Relevant academic research and scientific papers

Stereocontrol by intrinsic antiparallel double repulsion on diacetone-D-glucose template. Diastereoselective synthesis of 3(S)-isothiocyanato-3-deoxy-3-C-vinyl glucose via (3,3)-sigmatropic rearrangement of allylic thiocyanates

A stereoselective synthesis of the branched-chain sugar 3(S)-isothiocyanato-3-deoxy-3-C-vinyl glucose via (3,3)-sigmatropic rearrangement of allylic thiocyanates prepared from D-glucose is presented. The side chain at C-4 of the substrates 4-Z, 4-E and and 8-E is not a decisive factor for stereocontrol in the (3,3)-sigmatropic rearrangement of allylic thiocyanates, and the 1,2-O-isopropylidene group in each isomer profoundly affects the direction of the rearrangement.

Creation of quarternary stereocentres via [3,3]-sigmatropic rearrangement of allylic thiocyanates. A synthetic approach to (+)-myriocin

A stereoselective approach to the advanced precursor of (+)-myriocin, 3-deoxy-1,2:5,6-di-O-isopropylidene-3-methoxycarbonylamino-α-d-glucofuranose 3-C-carboxylic acid, via the [3,3]-sigmatropic rearrangement of allylic thiocyanates prepared from d-glucose is presented. From the observed results, supported by DFT calculations, we can conclude that the [3,3]-sigmatropic rearrangement of the thiocyanato group in allylic hexofuranosides is strongly influenced by the steric interaction of the 1,2-O-isopropylidene group in the transition states.