117320-21-5

Basic information

• Product Name: 2,3,4',5',6',7'-hexa-O-benzyl-4,5-O-benzyllidenevalidoxylamine B
• Synonyms: 2,3,4',5',6',7'-hexa-O-benzyl-4,5-O-benzyllidenevalidoxylamine B
• CAS NO: 117320-21-5
• Molecular Weight: 980.21
• Mol File: 117320-21-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2,3,4',5',6',7'-hexa-O-benzyl-4,5-O-benzyllidenevalidoxylamine B(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4',5',6',7'-hexa-O-benzyl-4,5-O-benzyllidenevalidoxylamine B(117320-21-5)
• EPA Substance Registry System: 2,3,4',5',6',7'-hexa-O-benzyl-4,5-O-benzyllidenevalidoxylamine B(117320-21-5)

Safety Data

• Hazardous Substances Data: 117320-21-5(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 119066-22-7 (1S)-(1,3/2,4)-1,2,3-triacetoxy-4-benzoyloxymethylcyclohex-5-ene 
• 119066-23-8 (1R,3R,6R,9S,10S)-9,10-dihydroxy-3-phenyl-2,4-dioxabicyclo<4.4.0>dec-7-ene 
• 119067-99-1 (-)-(1R,2R,3R,4S)-1-(hydroxymethyl)cyclohex-5-ene-2,3,4-triol 
• 90025-03-9 (1S)-(1,3,6/2)-4-acetoxymethyl-1,2,3-tri-O-acetyl-6-azido-4-cyclohexene-1,2,3-triol 
• 114779-28-1 (1R,3R,6R,9S,10S)-9,10-dibenzyloxy-3-phenyl-2,4-dioxabicyclo<4.4.0>dec-7-ene 
• 97747-51-8 (1R)-(-)-1,2,3-tri-O-acetyl-(1,3/2,4,6)-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 114779-32-7 1D-(1,3,6/2)-6-amino-4-benzyloxymethyl-1,2,3-tri-O-benzyltrihydroxycyclohex-4-ene 
• 114779-35-0 (1R,2S,5R,7R,8R,9R,10R)-8,9-dibenzyloxy-5-phenyl-4,6,11-trioxatricyclo<8.1.0.0^2.7>undecane 
• 114779-35-0 (1aR,2S,3S,3aR,5R,7aS,7bR)-2,3-Bis-benzyloxy-5-phenyl-hexahydro-1,4,6-trioxa-cyclopropa[a]naphthalene 

Downstream Products

• 37248-47-8 validamycin A 
• 86733-63-3 7,2'',3'',4'',6''-penta-O-acetyl-2,3,4',5',6',7'-hexa-O-benzylvalidamycin A 
• 86733-62-2 7-O-acetyl-2,3,4',5',6',7'-hexa-O-benzylvalidoxylamine A 
• 86733-61-1 2,3,4',5',6',7'-hexa-O-benzylvalidoxylamine A 
• 39318-73-5 validoxylamine B 
• 118968-13-1 4,7-di-O-acetyl-2,3,6,4',5',6',7'-hepta-O-benzylvalidoxylamine B 
• 118968-12-0 7-O-acetyl-2,3,6,4',5',6',7'-hepta-O-benzylvalidoxylamine B 
• 118968-11-9 2,3,6,4',5',6',7'-hepta-O-benzylvalidoxylamine B 
• 117295-72-4 2,3,4',5',6',7'-hexa-O-benzyl-4,7-O-benzylidene-6-p-toluenesulphenylvalidoxylamine A 
• 38665-10-0 (+)-validoxylamine A 
• 117295-70-2 Dithiocarbonic acid O-[(2R,4aS,5R,6S,7S,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-6-((1S,4R,5S,6S)-4,5,6-tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enylamino)-hexahydro-benzo[1,3]dioxin-5-yl] ester S-methyl ester 
• 100-52-7 benzaldehyde 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 108-95-2 phenol 

Relevant articles and documents

Synthetic studies on antibiotic validamycins. Part 13. Total synthesis of (+)-validamycins A and E, and related compounds

(+)-Validoxylamine A (1) has been completely synthesized by deoxygenation of the validoxylamine B derivative (6) through formation of the aziridine, nucleophilic displacement with toluenethiol, reduction with Raney nickel, and deprotection. The validoxylamine A derivative (10) obtained was convertible, by glycosylation followed by deprotection, into validamycins A (2), E (3), and their analogues, which constitutes a total synthesis thereof.

Total Synthesis of (+)-Validoxylamine A

(+)-Validoxylamine A was synthesized by selective deoxygenation of (+)-validoxylamine B derivative, which was obtained by the coupling of the partially protected (+)-valienamine and (1R,2S,5R,7R,8R,9R,10R)-8,9-dibenzyloxy-5-phenyl-4,6,11-trioxatricyclo8.