86733-61-1

Upstream product

• 114779-35-0 (1aR,2S,3S,3aR,5R,7aS,7bR)-2,3-Bis-benzyloxy-5-phenyl-hexahydro-1,4,6-trioxa-cyclopropa[a]naphthalene 
• 117295-72-4 2,3,4',5',6',7'-hexa-O-benzyl-4,7-O-benzylidene-6-p-toluenesulphenylvalidoxylamine A 
• 117320-21-5 2,3,4',5',6',7'-hexa-O-benzyl-4,5-O-benzyllidenevalidoxylamine B 
• 117295-71-3 (1S,2R,5R,7R,8S,10S)-8,9-dibenzyloxy-11-<(1S)-(1,4,6/5)-4,5,6-tribenzyloxy-3-benzyloxymethylcyclohex-2enyl>-5-phenyl-4,6-dioxa-11-azatricyclo<8.1.0.0.^2,7>undecane 
• 114779-32-7 1D-(1,3,6/2)-6-amino-4-benzyloxymethyl-1,2,3-tri-O-benzyltrihydroxycyclohex-4-ene 
• 100-39-0 benzyl bromide 
• 86733-60-0 Acetic acid (4aR,6S,7S,8S,8aR)-7-acetoxy-2-phenyl-6-((1S,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enylamino)-hexahydro-benzo[1,3]dioxin-8-yl ester 
• 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 
• 86756-42-5 2,3,4',5',6',7'-hexa-O-benzyl-4,7-O-benzylidenevalidoxylamine A 

Downstream Products

• 137063-35-5 2,3,4',5',6',7'-hexa-O-benzyl-7-O-triphenylmethylvalidoxylamine A 
• 86733-62-2 7-O-acetyl-2,3,4',5',6',7'-hexa-O-benzylvalidoxylamine A 
• 137063-36-6 2,3,4,4',5',6',7'-hepta-O-benzyl-7-O-triphenylmethylvalidoxylamine A 
• 137063-37-7 ((1R,2R,3S,4S,5S)-2,3,4-tris(benzyloxy)-5-(((1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)cyclohex-2-en-1-yl)amino)cyclohexyl)methanol 
• 139499-25-5 <(1S)-(1,2,4/3,5)-4-acetoxy-5-acetoxymethyl-2,3-dibenzyloxycyclohexyl><(1S)-(1,2,4/3,5)-2,3,4-tribenzyloxy-5-(benzyloxymethyl)cyclohexyl>amine 
• 37248-47-8 validamycin A 
• 102069-49-8 2'',3'',4'',6''-tetra-O-acetyl-2,3,4',5',6',7'-hexa-O-benzyl-7-deoxyvalidamycin A 
• 102069-48-7 2,3,4',5',6',7'-hexa-O-benzyl-7-deoxyvalidoxylamine A 
• 86733-63-3 7,2'',3'',4'',6''-penta-O-acetyl-2,3,4',5',6',7'-hexa-O-benzylvalidamycin A 
• 102069-47-6 2,3,4',5',6',7'-hexa-O-benzyl-7-deoxy-7-iodovalidoxylamine A 
• 139499-24-4 (2R)-(2,4/3,5)-4-acetoxy-5-acetoxymethyl-2,3-benzyloxycyclohexanone 
• 139499-20-0 N-acetyl-4,7-di-O-acetyl-2,3-di-O-benzylvalidamine 
• 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 

Relevant academic research and scientific papers

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.

Synthetic Studies on Antibiotic Validamycins. Part 11. Synthesis of Validamycin A

The antibiotic validamycin A (1a) has been synthesized for the first time (as its undeca-O-acetate) by glycosylation of the partially protected derivative (8) of the aglycone, validoxylamine A (2a), with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride (11), followed by deprotection, thereby establishing the structure previously assigned.The totally O-acetylated derivative (19) of 7-deoxyvalidamycin A has been synthesized in a similar fashion.

A FORMAL TOTAL SYNTHESIS OF VALIDAMYCIN A

Validamycin A has been prepared by a glycosidation of the partly blocked validoxylamine A, followed by deprotection.Since a racemic form of validoxylamine A has been totally synthesized, the synthesis of validamycin A is achieved by the present study.