223608-50-2

Basic information

• Product Name: N-(tert-butyloxycarbonyl)-4,5,6-tri-O-acetyl-valienamine-3-aldehyde
• CAS NO: 223608-50-2
• Molecular Weight: 399.398
• Mol File: 223608-50-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-(tert-butyloxycarbonyl)-4,5,6-tri-O-acetyl-valienamine-3-aldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: N-(tert-butyloxycarbonyl)-4,5,6-tri-O-acetyl-valienamine-3-aldehyde(223608-50-2)
• EPA Substance Registry System: N-(tert-butyloxycarbonyl)-4,5,6-tri-O-acetyl-valienamine-3-aldehyde(223608-50-2)

Safety Data

• Hazardous Substances Data: 223608-50-2(Hazardous Substances Data)

Upstream product

• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 108-24-7 acetic anhydride 
• 37248-47-8 validamycin A 

Downstream Products

• 223608-51-3 [7-3H]-N-(tert-butyloxycarbonyl)-4,5,6,7-tetra-O-acetyl-valienamine 
• 223608-52-4 N-(tert-butoxycarbonyl)-[7-3H]valienamine 
• 223608-55-7 [7-3H]valiolamine 
• 223608-57-9 [7-3H]valienamine 

Relevant articles and documents

Synthesis of [7-3H]valienamine, [7-3H]valienone, [7-3H]valiolamine and [7-3H]valiolone from validamycin A

To investigate the biosynthetic pathway to the cyclitol moieties of acarbose and validamycin A, [7-3H]valienamine, [7-3H]valienone, [7-3H]valiolamine and [7-3H]valiolone were synthesized as plausible precursors. Valienamine together with validamine was isolated from the degradation of validamycin A by Flavobacterium saccharophilum and served as starting material for the synthesis. Validamine was removed partially at the stage of tritylation and completely after the oxidation of the primary hydroxy group at C-7 to the aldehyde. The resulting valienamine aldehyde was reduced with tritiated sodium borohydride to produce [7-3H]valienamine. The latter was converted to [7-3H]valiolamine by a synthetic route described in the literature. The 3H-labeled amines were oxidized to [7-3H]valienone and [7-3H]valiolone, respectively, using 3,5-di-tert-butyl-1,2-bezoquinone (DBQ) followed by hydrolysis with oxalic acid.