128500-09-4

Upstream product

• 3587-60-8 Benzyloxymethyl chloride 
• 85798-11-4 (4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one 
• 85716-44-5 methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside 
• 6304-96-7 methyl 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-α-D-glucopyranoside 
• 6217-21-6 methyl 2,3,4-tri-O-acetyl-6-desoxy-α-D-xylo-hex-5-enopyranoside 
• 606930-14-7 (2S,3R,4S)-2,3,4-tris-benzyloxy-5-hydroxycyclohexan-1-one 
• 100-39-0 benzyl bromide 
• 13265-83-3 methyl 6-deoxy-α-D-xylo-hex-5-enopyranoside 
• 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 

Downstream Products

• 128500-10-7 1D-(1,3/2,6)-4-benzyloxymethyl-1,2,3-tri-O-benzyltrihydroxy-6-chlorocyclohex-4-ene 
• 128500-12-9 1D-(1,3/2,4)-1-O-acetyl-1-benzyloxymethyl-2,3,4-tri-O-benzyltetrahydroxycyclohex-5-ene 
• 75348-21-9 1D-(1,3,6/2)-6-azido-4-benzyloxymethyl-1,2,3-tri-O-benzyltrihydroxycyclohex-4-ene 
• 114779-32-7 1D-(1,3,6/2)-6-amino-4-benzyloxymethyl-1,2,3-tri-O-benzyltrihydroxycyclohex-4-ene 
• 38231-86-6 valienamine 

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%).

β-acarbose. I. The synthesis of 1-epivalienamine

Improvements and modifications to a literature procedure for the synthesis of multigram amounts of a derivative of 1-epivalienamine are described. As well, various other derivatives of 1-epivalienamine, of potential use in the synthesis of carba sugars, a

STEREOCONTROLLED SYNTHESIS OF (+)-VALIENAMINE

(+)-Valienamine, 1, constituent of antibiotics and α-glucosidase inhibitors, is synthesized through a simple and stereoselective procedure, starting from the easily available enone 3.A stereoselective access to 6-epivalienamine, 2, from the same precursor is also described.