64067-13-6 Usage
Description
(4-Nitrophenyl)methyl [5R-[5alpha,6alpha(R)]]-6-(1-hydroxyethyl)-3-[[2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate is a complex organic compound that serves as an intermediate in the synthesis of Thienamycin (T344270), a potent naturally produced antibiotic with broad-spectrum activity against both Gram-positive and Gram-negative bacteria. (4-nitrophenyl)methyl [5R-[5alpha,6alpha(R)]]-6-(1-hydroxyethyl)-3-[[2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate is characterized by its unique molecular structure, which includes a 1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate core, a 4-nitrophenylmethoxycarbonyl group, and a hydroxyethylthio side chain.
Uses
Used in Pharmaceutical Industry:
(4-Nitrophenyl)methyl [5R-[5alpha,6alpha(R)]]-6-(1-hydroxyethyl)-3-[[2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate is used as an intermediate in the synthesis of Thienamycin (T344270) for its potent antibiotic properties. Thienamycin exhibits excellent activity against a wide range of bacteria, including both Gram-positive and Gram-negative strains, and is resistant to bacterial β-lactamase enzymes, making it a valuable asset in the development of new antibiotics to combat drug-resistant infections.
Check Digit Verification of cas no
The CAS Registry Mumber 64067-13-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,4,0,6 and 7 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 64067-13:
(7*6)+(6*4)+(5*0)+(4*6)+(3*7)+(2*1)+(1*3)=116
116 % 10 = 6
So 64067-13-6 is a valid CAS Registry Number.
64067-13-6Relevant articles and documents
A new strategy for the synthesis of carbapenems. A formal total synthesis of (+)-thienamycin
Feigelson, Gregg B.
, p. 4747 - 4750 (2007/10/02)
A new approach to formation of the carbapenem ring system is presented. The key step involves the Lewis acid mediated cyclocondensation of a β-lactam nitrogen and the α-keto ester of a suitably disposed side-chain. The preparation of a known and pivotal intermediadate in the synthesis of thienamycin serves to demonstrate this strategy.
A Novel Ring-Closure Strategy for the Carbapenems: The Total Synthesis of (+)-Thienamycin
Hanessian, Stephen,Desilets, Denis,Bennani, Youssef L.
, p. 3098 - 3103 (2007/10/02)
Intramolecular Michael cyclization of an N--4-(3-nitro-2-propenyl)-3-oxoazetidin-2-one available in optically pure form leads to the corresponding carbapenam skeleton.Further elaboration via oxidative cleavage of an exocyclic nitromethylene group gives an advanced intermediate, which was transformed into (+)-thienamycin.The stereochemistry of the Michael cyclization and the pitfalls of protective group chemistry are discussed.
A DIRECT TRANSFORMATION OF BICYCLIC KETO ESTERS TO N-FORMIMIDOYL THIENAMYCIN
Shinkai, I.,Reamer, R. A.,Hartner, F. W.,Liu, T.,Sletzinger, M.
, p. 4903 - 4906 (2007/10/02)
A convenient direct transformation of p-nitrobenzyl 6-(1'-hydroxyethyl)-azabicyclo-(3.2.0)heptane-3,7-dione-2-carboxylate to N-formimidoyl thienamycin utilizing the silylated derivative of N-formimidoyl cysteamine is described.
