159173-40-7

Basic information

• Product Name: (2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-Methyl-3'-butenyl)-pyrrolidine
• Synonyms: (2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-Methyl-3'-butenyl)-pyrrolidine;(S)-tert-Butyl 2-((1R,2S)-1-hydroxy-2-methylbut-3-en-1-yl)pyrrolidine-1-carboxylate
• CAS NO: 159173-40-7
• Molecular Formula: C₁₄H₂₅NO₃
• Molecular Weight: 255.3532
• EINECS: -0
• Mol File: 159173-40-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 347.2±15.0 °C(Predicted)
• Appearance: /
• Density: 1.041±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 14.41±0.20(Predicted)
• CAS DataBase Reference: (2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-Methyl-3'-butenyl)-pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-Methyl-3'-butenyl)-pyrrolidine(159173-40-7)
• EPA Substance Registry System: (2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-Methyl-3'-butenyl)-pyrrolidine(159173-40-7)

Safety Data

• Hazardous Substances Data: 159173-40-7(Hazardous Substances Data)

Usage

General Description

(2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-methyl-3'-butenyl)-pyrrolidine is a chemical compound that belongs to the class of pyrrolidine compounds. It is a chiral compound with a specific stereochemistry. The compound has a tert-butoxycarbonyl (Boc) protecting group attached to the nitrogen atom, which makes it useful in organic synthesis. The presence of a hydroxy and a methyl group in the side chain of the pyrrolidine ring adds to its complexity and potential reactivity. (2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-methyl-3'-butenyl)-pyrrolidine's specific structure and functional groups make it an important intermediate in the synthesis of various bioactive molecules and pharmaceutical compounds.

Upstream product

• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 69610-41-9 Boc-L-Pro-H 
• 115186-37-3 tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate 
• 99438-30-9 (Z)-(+)-crotyldiisopinocampheyl borane 
• 99397-92-9 (Z)-(-)-crotylbis(isopinocampheyl)borane 
• 69611-02-5 (E)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 69611-01-4 (Z)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

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 
• 1415246-55-7 (S)-methyl 2-((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-2-((tert-butoxycarbonyl)amino)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoyl)-pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoate 
• 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 

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.

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A stepwise synthesis of dolastatin 10 starting from the dolaphenine residue is described. The chiral dola isoleuine and dolaproine residues were obtained by 5-step procedures from the corresponding N-Boc amino acid. The key steps are respectively the NaBH4 reduction of an allylic ketone and the addition of an achiral Z-crotylboronate on the N-Boc-L-prolinal. Peptidic couplings were efficiently realised with reagents developed in the laboratory.