ACETOXYSILYLOXYAZETIDINONE

PRODUCT IDENTIFICATION

CAS NO. 76855-69-1

ACETOXYAZETIDINONE

EINECS NO. 408-050-9
FORMULA C13H25NO4Si
MOL WT. 287.43

H.S. CODE

 

TOXICITY

 

SYNONYMS 4-AOSA; 4-AA;
(3R-(3alpha(R'),4beta))-4-(acetyloxy)-3-(1-(((1,1-dimethylethyl)dimethlsilyl)oxy) ethyl) azetidin-2-one; (3S,4R)-4-Acetoxy-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)azetidin-2-one; (3R,4R)-4-Acetoxy-3-((R)-1-(t-butyldimethylsilyloxy)ethyl)-2-azetidinone;
DERIVATION

 

CLASSIFICATION

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE white to yellowish crystalline powder
MELTING POINT

106 - 110 C

BOILING POINT

 

SPECIFIC GRAVITY

1.02

SOLUBILITY IN WATER Insoluble (soluble in ethanol, ether, toluene and acetonitrile)
pH  
VAPOR DENSITY

 

AUTOIGNITION

 

NFPA RATINGS

Health: 2 Flammability: 0 Reactivity: 0

REFRACTIVE INDEX

 

FLASH POINT

 

STABILITY

Stable under ordinary conditions

GENERAL DESCRIPTION & APPLICATIONS

Azetidine, (oxetane, or thietane) is a heterocyclic compound of 4-membered ring with nitrogen as its heteroatom replacing a carbon at one position. It is a cyclic amine containing three carbon atoms and one nitrogen atom. It is a clear liquid (boiling point 61 - 62 C) with an unpleasant ammonia-like odor. It is found in many pharmaceutical drugs such as Carmantadine, Fluzinamide, Mugineic acid, Azetomycins, Tazadolene, Cefsulodin monobactam, Dezinamide and Imipenem. Azetidine-2-carboxylic acid (abbreviated Aze) is a homologue of proline, an 4-membered ring structure alpha-amino acid. It is a toxic non-protein amino acid that is misincorporated into protein in place of proline; induces nonfunctional heat-shock proteins; inhibits acquired thermotolerance. Cyclic amine analogues are aziridine (3-member ring), pyrrolidine (5-member ring) and piperidine (6-member ring). And Aromatic analogs are pyrrole ( 5-member ring  with two double bonds), pyrroline (5-member ring with one double bond) and Azepine ( 7-member ring  with three double bonds).

Acetoxysilyloxyazetidinone is an intermediate to produce carbapenem family synthetic beta-lactam antibiotics (ertapenem, imipenem/cilastatin, meropenem). There are two optically active hydrogen atoms on the lactam ring, which is the key factor of this molecule structure.

SALES SPECIFICATION

APPEARANCE

white to yellowish crystalline powder

PURITY

98.5% min

MELTING POINT

106 - 110 C

OPTICAL ROTATION

+53° ~ +56° (C=0.5, toluene)

OPTICAL PURITY

99.0% min

WATER

0.2% max

RELATED SUBSTANCES

0.8% max

TRANSPORTATION
PACKING

 

HAZARD CLASS  
UN NO.  
PRICES

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