911122-63-9

Upstream product

• 1003-03-8 Cyclopentamine 
• 195315-66-3 3-deoxy-1,2:5,6-di-O-isopropylidene-3-isothiocyanato-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 
• 195315-67-4 3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-(E)-(2-thiocyanatoethylidene)-α-D-glucofuranose 
• 195315-64-1 3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-(Z)-(2-thiocyanatoethylidene)-α-D-glucofuranose 
• 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 

Downstream Products

• 195315-76-5 3-deoxy-3-(N-cyclopentylthiocarboxamido)-1,2-O-isopropylidene-3-C-vinyl-α-D-glucofuranose 

Relevant academic research and scientific papers

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.