120205-54-1

Basic information

• Product Name: 1-Pyrrolidinecarboxylic acid, 2-[(1R,2R)-1-Methoxy-2-Methyl-3-oxo-3-[[(1S)-2-phenyl-1-(2-thiazolyl)ethyl]aMino]propyl]-, 1,1-diMethylethyl ester, (2S)-
• Synonyms: 1-Pyrrolidinecarboxylic acid, 2-[(1R,2R)-1-Methoxy-2-Methyl-3-oxo-3-[[(1S)-2-phenyl-1-(2-thiazolyl)ethyl]aMino]propyl]-, 1,1-diMethylethyl ester, (2S)-
• CAS NO: 120205-54-1
• Molecular Weight: 473.637
• Mol File: 120205-54-1.mol
• Article Data: 20

Chemical Properties

• CAS DataBase Reference: 1-Pyrrolidinecarboxylic acid, 2-[(1R,2R)-1-Methoxy-2-Methyl-3-oxo-3-[[(1S)-2-phenyl-1-(2-thiazolyl)ethyl]aMino]propyl]-, 1,1-diMethylethyl ester, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylic acid, 2-[(1R,2R)-1-Methoxy-2-Methyl-3-oxo-3-[[(1S)-2-phenyl-1-(2-thiazolyl)ethyl]aMino]propyl]-, 1,1-diMethylethyl ester, (2S)-(120205-54-1)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylic acid, 2-[(1R,2R)-1-Methoxy-2-Methyl-3-oxo-3-[[(1S)-2-phenyl-1-(2-thiazolyl)ethyl]aMino]propyl]-, 1,1-diMethylethyl ester, (2S)-(120205-54-1)

Safety Data

• Hazardous Substances Data: 120205-54-1(Hazardous Substances Data)

Usage

Molecular structure

The compound is a derivative of pyrrolidinecarboxylic acid with a complex structure containing various functional groups.

Functional groups

Methoxy group, methyl group, and thiazolyl group.

Stereochemistry

The compound is the (2S)-diastereomer of the 1,1-dimethylethyl ester of the carboxylic acid.

Application

Commonly used in the pharmaceutical industry for drug development and synthesis.

Interest to researchers

Its specific structure and properties make it of interest to scientists working in organic chemistry and pharmaceuticals.

Upstream product

• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 115186-37-3 tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate 
• 69610-41-9 Boc-L-Pro-H 
• 120205-50-7 N-Boc-(2R,3R,4S)-dolaproine 
• 158189-10-7 (+/-)-Boc-dolaphenine 
• 135383-60-7 (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethanamine, hydrochloride salt 
• 120205-51-8 tert-butyl N-[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]carbamate 
• 130199-65-4 (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethan-1-amine 
• 1369427-40-6 (2R,3R)-3-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropionic acid dicyclohexylamine salt 
• 122-78-1 phenylacetaldehyde 
• 1207946-42-6 (S)-N-(2-phenylethylidene)-tert-butylsulfinamide 
• 1329627-20-4 (S)-2-methyl-N-((S)-2-phenyl-1-(thiazol-2-yl)ethyl)propane-2-sulfinamide 

Downstream Products

• 159173-45-2 (3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe 
• 110417-88-4 dolastatin 10 
• 135383-62-9 Boc-(S)-Val-(3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe 
• 148597-90-4 Boc-(3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe 
• 148692-26-6 Z-Val-Dil-Dap-Doe 
• 1438851-43-4 tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-{[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino}-3-thioxopropyl]pyrrolidine-1-carboxylate 
• 1436391-86-4 2-methylalanyl-N-[(3R,4S,5S)-3-methoxy-1-{(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-{[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino}propyl]pyrrolidin-1-yl}-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide 

Relevant articles and documents

The dolastatins. 21. Synthesis, X-ray crystal structure, and molecular modeling of (6R)-isodolastatin 10

A practical synthesis of (6R)-isodolastatin 10 (1b) was devised, the X-ray crystal structure was determined, and this chiral isomer was found to have antineoplastic activity comparable to dolastatin 10 (1a).

CONJUGATE OF MONOMETHYL AURISTATIN F AND TRASTUZUMAB AND ITS USE FOR THE TREATMENT OF CANCER

The present invention relates to an antibody-drug-conjugate or pharmaceutical composition comprising the same. From one aspect, the invention relates to an antibody-drug-conjugate (ADC) comprising an antibody consisting of the Trastuzumab or a biosimilar thereof, said antibody being conjugated to at least one drug consisting of a monomethyl auristatin F derivative. The invention also comprises method of treatment of cancer comprising administering to the subject an effective amount of said antibody-drug-conjugate or composition comprising the same.

A practical approach to asymmetric synthesis of dolastatin 10

Dolastatin 10, an antineoplastic agent for cancer chemotherapy, is a linear peptide possessing N,N-dimethyl Val-OH, l-valine, (3R,4S,5S)-dolaisoleucine, (2R,3R,4S)-dolaproine and (S)-dolaphenine. Our efficient synthesis includes the following three key features: (1) SmI2-induced cross-coupling was employed to couple aldehyde 11 with (S)-N-tert-butanesulfinyl imine 12 to generate the required stereocenters of Dap (7); (2) asymmetric addition of chiral N-sulfinyl imine 10 provided a straightforward approach to the synthesis of the protected Doe ((S,S)-8); (3) a practical method to the key subunit Val-Dil (24a) has been established as an alternative synthetic route for the synthesis of this challenging chemical structure.