68108-50-9

Basic information

• Product Name: (1S)-(+)-(1,2,4/3,5)-1-acetamido-2,3,4-triacetoxy-5-acetoxymethylcyclohexane
• Synonyms: (1S)-(+)-(1,2,4/3,5)-1-acetamido-2,3,4-triacetoxy-5-acetoxymethylcyclohexane
• CAS NO: 68108-50-9
• Molecular Weight: 387.387
• Mol File: 68108-50-9.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: (1S)-(+)-(1,2,4/3,5)-1-acetamido-2,3,4-triacetoxy-5-acetoxymethylcyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-(+)-(1,2,4/3,5)-1-acetamido-2,3,4-triacetoxy-5-acetoxymethylcyclohexane(68108-50-9)
• EPA Substance Registry System: (1S)-(+)-(1,2,4/3,5)-1-acetamido-2,3,4-triacetoxy-5-acetoxymethylcyclohexane(68108-50-9)

Safety Data

• Hazardous Substances Data: 68108-50-9(Hazardous Substances Data)

Upstream product

• 38665-10-0 (+)-validoxylamine A 
• 108-24-7 acetic anhydride 
• 97747-53-0 (1S,2S,3R,4R,6S)-4-(acetoxymethyl)-6-azidocyclohexane-1,2,3-triyl triacetate 
• 5040-08-4 1,2-O-isopropylidene-α-D-xylo-5-hexulofuranurono-6,3-lactone 
• 70838-35-6 DL-(1,3/2,4,6)-1,2,3-tri-O-acetyl-4-bromo-6-bromomethyl-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 
• 32780-32-8 validamine 
• 64-19-7 acetic acid 
• 90025-01-7 (1R,2S,6S,7S,9R)-(-)-7-amino-4,4,12,12-tetramethyl-3,5,11,13-tetraoxatricyclo<7.4.0.0^2,6>tridecane 
• 124492-65-5 N-((1S,2S,3S,4R,5R)-2,3,4-Trihydroxy-5-hydroxymethyl-cyclohexyl)-acetamide 
• 74517-36-5 tetra-O-acetyl-(1,3,5/2,4)-2-bromo-5-hydroxymethyl-1,3,4-cyclohexanetriol 
• 117683-13-3 methyl DL-(1,3,5/2,4)-2,3,4-triacetoxy-5-bromocyclohexane-1-carboxylate 

Downstream Products

• 32780-31-7 DL-validamine hydrochloride 
• 124492-65-5 D,L-(1,3,4/2,6)-4-acetamido-6-hydroxymethyl-1,2,3-cyclohexanetriol (N-acetyl-D,L-validamine) 
• 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 N-((1S,2S,3S,4R,5R)-2,3,4-Trihydroxy-5-hydroxymethyl-cyclohexyl)-acetamide 
• 32780-32-8 validamine 

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.

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.

Enantiospecific Syntheses of Penta-N,O,O,O,O-acetylvalidamine and Penta-N,O,O,O,O-acetyl-2-epi-validamine

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