106988-93-6

Upstream product

• 100-39-0 benzyl bromide 
• 106988-92-5 1L-(1,2,4/3)-2,3,4-tri-O-benzyl-1-C-(hydroxymethyl)-5-cyclohexen-1,2,3,4-tetrol 
• 227930-72-5 (1D)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-C-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3,4-tetrol 
• 110205-68-0 1,3,4,5-tetra-O-benzyl-6,7-dideoxy-L-xylo-hept-6-en-2-ulose 
• 227930-71-4 3,4,5-tri-O-benzyl-6-C-[(benzyloxy)methyl]-1,2,7,8-tetradeoxy-D-gluco-octa-1,7-dienitol 
• 85798-11-4 (4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one 
• 106988-91-4 1L-(1,2,4/3)-2,3,4-tri-O-benzyl-1-C-(5-methyl-1,3,5-dithiazinan-2-yl)-5-cyclohexen-1,2,3,4-tetrol 

Relevant academic research and scientific papers

Carbasaccharides via ring-closing alkene metathesis. A synthesis of (+)- valienamine from D-glucose

(+)-Valienamine (16) was prepared in seven steps and in an overall yield of 17% from commercially available 2,3,4,6-tetra-O-benzyl-D-glucopyranose. Stereoselective addition of vinylmagnesium bromide to the 1,3,4,5-tetra-O- benzyl-6,7-dideoxy-L-xylo-hept-6-en-2-ulose (2) gave diene 3 (86%). Ring- closing alkene metathesis of 3 in the presence of 0.15 equiv, of Grubb's catalyst 1 gave the cyclohexene 4 (58%), that was converted into (+)- valienamine (16) in three steps and in 47% yield. Similarly, ring-closing alkene metathesis of the D-mannose-derived diene 20 gave the cyclohexene 21 (89%).