159173-43-0

Basic information

• Product Name: (2S,1'R,2'S)-N-(tert-butoxycarbonyl)- 2-(1'-Methoxy-2'-Methyl-3'-butenyl)- pyrrolidine
• Synonyms: (S)-tert-butyl 2-((1R,2S)-1-methoxy-2-methylbut-3-enyl)pyrrolidine-1-carboxylate;(2S,1'R,2'S)-N-(tert-butoxycarbonyl)- 2-(1'-Methoxy-2'-Methyl-3'-butenyl)- pyrrolidine
• CAS NO: 159173-43-0
• Molecular Formula: C₁₅H₂₇NO₃
• Molecular Weight: 269.37978
• Mol File: 159173-43-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 328.1±25.0 °C(Predicted)
• Appearance: /
• Density: 0.996±0.06 g/cm3(Predicted)
• PKA: -2.10±0.40(Predicted)
• CAS DataBase Reference: (2S,1'R,2'S)-N-(tert-butoxycarbonyl)- 2-(1'-Methoxy-2'-Methyl-3'-butenyl)- pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,1'R,2'S)-N-(tert-butoxycarbonyl)- 2-(1'-Methoxy-2'-Methyl-3'-butenyl)- pyrrolidine(159173-43-0)
• EPA Substance Registry System: (2S,1'R,2'S)-N-(tert-butoxycarbonyl)- 2-(1'-Methoxy-2'-Methyl-3'-butenyl)- pyrrolidine(159173-43-0)

Safety Data

• Hazardous Substances Data: 159173-43-0(Hazardous Substances Data)

Usage

General Description

The chemical compound "(2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-methoxy-2'-methyl-3'-butenyl)-pyrrolidine" is a pyrrolidine derivative with a tert-butoxycarbonyl (Boc) protecting group. It has a specific stereochemistry, indicated by the (2S,1'R,2'S) notation, and is made up of a pyrrolidine ring with a substituted butenyl group. The compound is commonly used in organic synthesis as a chiral building block for the preparation of various pharmaceuticals and agrochemicals. The presence of the Boc protecting group makes it suitable for use in peptide synthesis and as a versatile intermediate in the production of complex organic molecules.

Upstream product

• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 74-88-4 methyl iodide 
• 69610-41-9 Boc-L-Pro-H 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 159173-40-7 (2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-methyl-3'-butenyl)-pyrrolidine 
• 115186-37-3 tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate 

Downstream Products

• 161485-88-7 methyl (S)-2-((2R,3R)-3-methoxy-2-methyl-3-((S)-pyrrolidin-2-yl)propanamido)-3-phenylpropanoate 2,2,2-trifluoroacetate 
• 1369427-27-9 (S)-2-((2R,3R)-3-((S)-1-((6S,9S,12S,13R)-12-((S)-sec-butyl)-6,9-diisopropyl-13-methoxy-2,2,5,11-tetramethyl-4,7,10-trioxo-3-oxa-5,8,11-triazapentadecan-15-oyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoic acid 
• 1415246-61-5 (S)-methyl 2-((2R,3R)-3-((S)-1-((6S,9S,12S,13R)-12-((S)-sec-butyl)-6,9-diisopropyl-13-methoxy-2,2,5,11-tetramethyl-4,7,10-trioxo-3-oxa-5,8,11-triazapentadecan-15-oyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoate 

Relevant articles and documents

Synthesis and biological activity evaluation of dolastatin 10 analogues with N-terminal modifications

We have described the synthesis of the two complex units (2R,3R,4S)-dolaproine (Dap) and (3R,4S,5S)-dolaisoleuine (Dil) of dolastatin 10 from natural amino acids. The stereoselective syntheses of N-Boc-Dap (4a) and N-Boc-(2S)-iso-Dap (4b) were performed by employing crotylation of N-Boc-L-prolinal as a key step. Barbier-type allylation of N-Boc-L-isoleucinal provided a mild and convenient approach for the synthesis of N-Boc-Dil (5a) and N-Boc-(3S)-iso-Dil (5b). Ten dolastatin 10 analogues have been designed and synthesized with N-terminal modifications based on the known compound monomethylauristatin F (MMAF, 3). In comparison with MMAF (3), four of the compounds showed enhanced potency against HCT 116 human colon cancer cells in?vitro.

CYTOTOXIC PEPTIDES AND ANTIBODY DRUG CONJUGATES THEREOF

The present invention is directed to cytotoxic pentapeptides, to antibody drug conjugates thereof, and to methods for using the same to treat cancer.