183660-36-8

Basic information

• Product Name: Acetic acid (1S,2S,3R,4S,6R)-4,6-bis-benzyloxycarbonylamino-3-[(2R,3R,4R,5R,6R)-4,5-diacetoxy-3-benzyloxycarbonylamino-6-(benzyloxycarbonylamino-methyl)-tetrahydro-pyran-2-yloxy]-2-(2-oxo-ethoxy)-cyclohexyl ester
• Synonyms: Acetic acid (1S,2S,3R,4S,6R)-4,6-bis-benzyloxycarbonylamino-3-[(2R,3R,4R,5R,6R)-4,5-diacetoxy-3-benzyloxycarbonylamino-6-(benzyloxycarbonylamino-methyl)-tetrahydro-pyran-2-yloxy]-2-(2-oxo-ethoxy)-cyclohexyl ester
• CAS NO: 183660-36-8
• Molecular Weight: 1027.05
• Mol File: 183660-36-8.mol

Chemical Properties

• CAS DataBase Reference: Acetic acid (1S,2S,3R,4S,6R)-4,6-bis-benzyloxycarbonylamino-3-[(2R,3R,4R,5R,6R)-4,5-diacetoxy-3-benzyloxycarbonylamino-6-(benzyloxycarbonylamino-methyl)-tetrahydro-pyran-2-yloxy]-2-(2-oxo-ethoxy)-cyclohexyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid (1S,2S,3R,4S,6R)-4,6-bis-benzyloxycarbonylamino-3-[(2R,3R,4R,5R,6R)-4,5-diacetoxy-3-benzyloxycarbonylamino-6-(benzyloxycarbonylamino-methyl)-tetrahydro-pyran-2-yloxy]-2-(2-oxo-ethoxy)-cyclohexyl ester(183660-36-8)
• EPA Substance Registry System: Acetic acid (1S,2S,3R,4S,6R)-4,6-bis-benzyloxycarbonylamino-3-[(2R,3R,4R,5R,6R)-4,5-diacetoxy-3-benzyloxycarbonylamino-6-(benzyloxycarbonylamino-methyl)-tetrahydro-pyran-2-yloxy]-2-(2-oxo-ethoxy)-cyclohexyl ester(183660-36-8)

Safety Data

• Hazardous Substances Data: 183660-36-8(Hazardous Substances Data)

Upstream product

• 183660-32-4 Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-6-((1R,2S,3S,4R,6S)-3-acetoxy-4,6-bis-benzyloxycarbonylamino-2-hydroxy-cyclohexyloxy)-5-benzyloxycarbonylamino-2-(benzyloxycarbonylamino-methyl)-tetrahydro-pyran-4-yl ester 
• 3947-65-7 neomycin A 
• 22854-75-7 N,N',N'',N'''-tetra(benzyloxycarbonyl)neamine 
• 119-04-0 neomycin B 
• 183660-34-6 Acetic acid (1S,2S,3R,4S,6R)-2-allyloxy-4,6-bis-benzyloxycarbonylamino-3-[(2R,3R,4R,5R,6R)-4,5-diacetoxy-3-benzyloxycarbonylamino-6-(benzyloxycarbonylamino-methyl)-tetrahydro-pyran-2-yloxy]-cyclohexyl ester 

Downstream Products

• 267661-98-3 5-O-hydroxyethyl-4,3',4'-tri-O-acetyl-1,3,2',6'-tetra-N-benzyloxycarbonylneamine 

Relevant articles and documents

Rapid combinatorial synthesis of aminoglycoside antibiotic mimetics: Use of a polyethylene glycol-linked amine and a neamine-derived aldehyde in multiple component condensation as a strategy for the discovery of new inhibitors of the HIV RNA Rev responsive element

A library of neomycin B mimetics has been prepared rapidly without chromatography using a neamine-derived aldehyde, tert-butyl isocyanide or isocyanoacetic acid methyl ester, a glycine-conjugated polyethylene glycol (PEG) methyl ether, and various Cbz-N-protected amino acids as substrates in a Ugi-type one-pot reaction. The product linked to PEG was isolated by precipitation in ether. A simultaneous base-catalyzed hydrolysis and de-O-acetylation followed by hydrogenation provided an easy access to a library of neomycin B mimetics, which were screened for binding to the Rev responsive element of HIV mRNA (RRE). Several products were found to be more active than neamine with the IC50 values in the micromolar range.