227930-71-4

Upstream product

• 1826-67-1 vinyl magnesium bromide 
• 110205-68-0 1,3,4,5-tetra-O-benzyl-6,7-dideoxy-L-xylo-hept-6-en-2-ulose 

Downstream Products

• 1064262-58-3 C₃₇H₃₉IO₅ 
• 227930-76-9 (1L)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-[(benzyloxycarbonyl)amino]-6-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3-triol 
• 227930-75-8 (1D)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-C-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3,4-tetrol 
• 106988-93-6 1L-(1,2,4/3)-1,2,3,4-tetra-O-benzyl-1-C-(benzyloxymethyl)-5-cyclohexen-1,2,3,4-tetrol 
• 118968-04-0 (1L)-(,3,4/2)-4-acetamido-1,2,3-tri-O-benzyl-4-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3-triol 
• 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 
• 128500-09-4 (1D)-(1,3/2,4)-1,2,3-tri-O-benzyl-4-C-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3,4-tetrol 

Relevant academic research and scientific papers

Stereospecific synthesis of eight-membered polyhydroxy carbocycles via TIBAL-promoted claisen rearrangement

The stereoselective synthesis of novel eight-membered polyhydroxy carbocycles was achieved from D-glucose via mercuriocyclization and triisobutylaluminum (TIBAL)-promoted Claisen rearrangement. Along with rearrangement, TIBAL also promoted debenzylation a

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%).