139499-19-7

Basic information

• Product Name: 2,3,4,7-tetra-O-benzylvalidamine
• CAS NO: 139499-19-7
• Molecular Weight: 537.699
• Mol File: 139499-19-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2,3,4,7-tetra-O-benzylvalidamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,7-tetra-O-benzylvalidamine(139499-19-7)
• EPA Substance Registry System: 2,3,4,7-tetra-O-benzylvalidamine(139499-19-7)

Safety Data

• Hazardous Substances Data: 139499-19-7(Hazardous Substances Data)

Upstream product

• 37248-47-8 validamycin A 
• 38665-10-0 (+)-validoxylamine A 
• 124330-57-0 (2R,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-[(benzyloxy)methyl]cyclohexanone 
• 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 

Downstream Products

• 124330-55-8 N-((1S,2S,3S,4R,5R)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-cyclohexyl)-acetamide 
• 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 
• 139877-35-3 bis<(1S)-(1,2,4/3,5)-2,3,4-tribenzyloxy-5-(benzyloxymethyl)cyclohexyl>amine 

Relevant articles and documents

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.

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