159173-40-7

Usage

Uses

Used in Organic Synthesis:
(2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-methyl-3'-butenyl)-pyrrolidine is used as an intermediate in organic synthesis for the preparation of various bioactive molecules and pharmaceutical compounds. Its specific structure and functional groups make it a valuable building block in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-methyl-3'-butenyl)-pyrrolidine is used as a key intermediate in the development of new drugs. Its unique stereochemistry and functional groups allow for the creation of novel therapeutic agents with potential applications in treating various diseases and medical conditions.

Upstream product

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

Downstream Products

• 745017-94-1 (S)-2-((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-N,3-dimethyl-2-((S)-3-methyl-2-(methylamino)butanamido)butanamido)-3-methoxy-5-methylheptanoyl)-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 
• 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 academic research and scientific papers

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.

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.

Stereoselective synthesis of the dolastatin units by organotrifluoroborates additions to α-amino aldehydes

Dolastatin units were synthesized from the 1,2-addition reactions of potassium allyl or crotyltrifluoroborate salts to aldehyde derivatives from natural amino acids. The reactions were carried out in presence of a phase-transfer catalyst in a biphasic medium at room temperature and excellent yields (>89-93%) and stereoselective (>90:10 to 98:2) were obtained. The dolastatin units 8 and 14a-b were obtained after three steps in good overall yields (50-62%).

Substrate-controlled Crotylboration from N-(tert-Butoxycarbonyl)amino Aldehydes

Chiral or achiral (Z)-crotylorganoboron compounds add preferentially anti to N-(tert-butoxacrbonyl)amino aldehydes.N-(tert-Butoxycarbonyl)prolinal 3 presents a remarkably high diastereofacial selectivity.Double stereodifferentiation, starting from compoun