86756-42-5

Upstream product

• 37248-47-8 validamycin A 
• 38665-10-0 (+)-validoxylamine A 
• 1316288-57-9 C₂₁H₂₉NO₈ 
• 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 
• 114779-35-0 (1aR,2S,3S,3aR,5R,7aS,7bR)-2,3-Bis-benzyloxy-5-phenyl-hexahydro-1,4,6-trioxa-cyclopropa[a]naphthalene 
• 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 
• 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 
• 117295-72-4 2,3,4',5',6',7'-hexa-O-benzyl-4,7-O-benzylidene-6-p-toluenesulphenylvalidoxylamine A 
• 86733-60-0 4,7-O-benzylidenevalidoxylamine A hexa-O-acetate 

Downstream Products

• 86733-61-1 2,3,4',5',6',7'-hexa-O-benzylvalidoxylamine 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 
• 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 
• 110391-10-1 (4R,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-2-cyclohexen-1-one 
• 124330-56-9 N-acetyl-2,3-di-O-benzyl-4,7-O-benzylidenevalidamine 
• 124330-58-1 (1R,3R,6R,9R,10S)-9,10-dibenzyloxy-3-phenyl-2,4-dioxabicyclo<4.4.0>decan-8-one 
• 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 
• 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 
• 102069-47-6 2,3,4',5',6',7'-hexa-O-benzyl-7-deoxy-7-iodovalidoxylamine 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 
• 86733-62-2 7-O-acetyl-2,3,4',5',6',7'-hexa-O-benzylvalidoxylamine A 

Relevant academic research and scientific papers

Pseudoglycosyltransferase catalyzes nonglycosidic C-N coupling in validamycin a biosynthesis

Glycosyltransferases are ubiquitous in nature. They catalyze a glycosidic bond formation between sugar donors and sugar or nonsugar acceptors to produce oligo/polysaccharides, glycoproteins, glycolipids, glycosylated natural products, and other sugar-containing entities. However, a trehalose 6-phosphate synthase-like protein has been found to catalyze an unprecedented nonglycosidic C-N bond formation in the biosynthesis of the aminocyclitol antibiotic validamycin A. This dedicated 'pseudoglycosyltransferase catalyzes a condensation between GDP-valienol and validamine 7-phosphate to give validoxylamine A 7′-phosphate with net retention of the 'anomeric configuration of the donor cyclitol in the product. The enzyme operates in sequence with a phosphatase, which dephosphorylates validoxylamine A 7′-phosphate to validoxylamine A.

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.

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.