68108-50-9

Upstream product

• 38665-10-0 (+)-validoxylamine A 
• 108-24-7 acetic anhydride 
• 97747-51-8 (1R)-(-)-1,2,3-tri-O-acetyl-(1,3/2,4,6)-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol 
• 74517-36-5 tetra-O-acetyl-(1,3,5/2,4)-2-bromo-5-hydroxymethyl-1,3,4-cyclohexanetriol 
• 69982-68-9 endo-3-acetoxy-endo-5-acetoxymethyl-exo-2-bromo-7-oxabicyclo<2.2.1>heptane 
• 74517-36-5 tetra-O-acetyl-(1,2/3,4,5)-2-bromo-5-hydroxymethyl-1,3,4-cyclohexanetriol 
• 108794-45-2 DL-(1,2/3,4,5)-3,4-diacetoxy-5-acetoxymethyl-1,2-epoxycyclohexane 
• 70838-35-6 DL-(1,3/2,4,6)-1,2,3-tri-O-acetyl-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol 
• 117683-13-3 methyl DL-(1,3,5/2,4)-2,3,4-triacetoxy-5-bromocyclohexane-1-carboxylate 
• 70878-41-0 DL-1,2,3-tri-O-acetyl-(1,3/2,4,6)-6-acetoxymethyl-4-bromo-1,2,3-cyclohexanetriol 

Downstream Products

• 32780-32-8 validamine 
• 124492-65-5 N-((1S,2S,3S,4R,5R)-2,3,4-Trihydroxy-5-hydroxymethyl-cyclohexyl)-acetamide 
• 86195-51-9 (-)-validamine hydrochloride 
• 32780-31-7 (+)-validamine hydrochloride 
• 73410-97-6 1D-2-O-β-D-glucopyranosyl-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol 
• 73410-97-6 2-O-β-D-glucopyranosyl-1L-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol 
• 73619-36-0 1D-1,7-O-benzylidene-3,4-N,O-carbonyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol 
• 73619-36-0 1L-1,7-O-benzylidene-3,4-N,O-carbonyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol 
• 73619-26-8 DL-(1,3,4/2,6)-4-benzyloxycarbonylamino-6-hydroxymethyl-1,2,3-cyclohexanetriol 
• 124492-65-5 D,L-(1,3,4/2,6)-4-acetamido-6-hydroxymethyl-1,2,3-cyclohexanetriol (N-acetyl-D,L-validamine) 
• 32780-31-7 DL-validamine hydrochloride 

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.

Total synthesis of (±)-2-Epi-validamine

(±)-Validamine and its epimers, (±)-2-epi-validamine (dl-5a-carba-α-mannopyranosylamine) and (±)-2-epi-3-epi-validamine (dl-5a-carba-α-altropyranosylamine) were synthesized from a poly-functionalized bicyclolactam that obtained by a base-catalyzed Diels-A

A novel and concise synthesis of (±) 2-epi-Validamine

(±) 2-epi-Validamine has been synthesized in five steps by the chemical manipulation of the bicyclic lactone cycloadduct of ethyl coumalate and vinylene carbonate.

A novel synthesis of (±) 2-epi-validamine

(±) 2-epi-Validamine is synthesised in five steps by the chemical manipulation of bicyclic lactone cycloadduct of ethyl coumalate and vinylene carbonate.

Stereoselective conversion of D-glucuronolactone into pseudosugar: Synthesis of pseudo-α-D-glucopyranose, pseudo-β-D-glucopyranose, and validamine

Two optically active pseudo-sugars, pseudo-α-D-glucopyranose (12) and pseudo-β-D-glucopyranose (13), were synthesized from D-glucuronolactone in favorable overall yields by using a stereoselective nitromethane addition reaction and a reductive elimination of an ethoxyethoxyl moiety with NaBH4 as key steps. Furthermore, a biologically active pseudo-aminosguar, validamine (18) was efficiently synthesized via a substitution reaction for an acetoxyl group at the β-position of nitro group in a nitrocyclitol derivative (14) which was prepared from a synthetic intermediate (9) of pseudo-d-glucopyranoses (12,13).

A Stereodivergent Access to Naturally Occurring Aminocarbasugars from (Phenylsulfonyl)-7-oxabicycloheptane Derivatives. Total Synthesis of Penta-N,O-acetyl-(+/-)-validamine and Its C1 and C2 Stereoisomers

The total syntheses of the antibiotic component validamine 1 and its three diastereomers 2-4 have been accomplished as their racemic penta-N,O-acetates via stereocontrolled nucleophilic epoxidation of polyhydroxylated cyclohexenyl sulfones, obtained from

Syntheses of pseudo-α-D-glucopyranose, pseudo-β-D-glucopyranose, and validamine from D-glucuronolactone

Using a stereoselective nitromethane addition and a reductive elimination of an ethoxyethoxyl moiety with NaBH4 as key steps, two optically active pseudo-sugars, pseudo-α-D-glucopyranose and pseudo-β-D-glucopyranose, were synthesized from D-glucuronolactone in favorable overall yield. Furthermore, a biologically active pseudo-aminosugar, validamine, was synthesized via a substitution reaction for an acetoxyl group at the β-position of the nitro group in the nitrocyclitol derivative which was prepared from a synthetic intermediate of pseudo-D-glucopyranose.

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