118968-04-0

Upstream product

• 108-24-7 acetic anhydride 
• 86756-42-5 (4aR,6S,7S,8S,8aR)-7,8-bis(benzyloxy)-2-phenyl-N-((1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)cyclohex-2-en-1-yl)hexahydro-4H-benzo[d][1,3]dioxin-6-amine 
• 124330-54-7 (1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-N-((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)cyclohex-2-enamine 
• 114779-32-7 1D-(1,3,6/2)-6-amino-4-benzyloxymethyl-1,2,3-tri-O-benzyltrihydroxycyclohex-4-ene 
• 75-36-5 acetyl chloride 
• 90025-03-9 (1S)-(1,3,6/2)-4-acetoxymethyl-1,2,3-tri-O-acetyl-6-azido-4-cyclohexene-1,2,3-triol 
• 100-39-0 benzyl bromide 
• 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 
• 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 
• 99695-34-8 (1R,2S,3S,4R)-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol 
• 75348-21-9 1D-(1,3,6/2)-6-azido-4-benzyloxymethyl-1,2,3-tri-O-benzyltrihydroxycyclohex-4-ene 
• 75-24-1 trimethylaluminum 
• 86733-61-1 2,3,4',5',6',7'-hexa-O-benzylvalidoxylamine A 

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%).

Cleavage of Validoxylamine A Derivatives with N-Bromosuccinimide: Preparation of Blocked Synthons Useful for the Construction of Carba-oligosaccharides Composed of Imino-Linkages

Reaction of validoxylamine A and several of its derivatives with N-bromosuccinimide proceeded through cleavage of the imino bonds to give rise to the synthetically useful blocked derivatives of valienamine and validamine, and the cyclohexanone and cyclohe

SYNTHETIC STUDIES ON ANTIBIOTIC VALIDAMYCINS. PART 12. TOTAL SYNTHESIS OF (+)-VALIDAMYCIN B AND (+)-VALIDOXYLAMINE B

The first complete synthesis of validamycin B (1a) and validoxylamine B (2a) is reported; coupling of the epoxide (12) and the partially protected derivative (16) of (+)-valienamine, followed by deprotection, gives (1a), which was identified from the 1H n