377779-91-4

Upstream product

• 184434-21-7 2-methyl-2-(1-methylindol-3-yl)propionaldehyde 
• 7677-24-9 trimethylsilyl cyanide 
• 56613-80-0 D-2-phenylglycinol 
• 603-76-9 1-methylindole 
• 429-41-4 tetrabutyl ammonium fluoride 
• 184434-20-6 2-methyl-2-(1-methyl-1H-indole-3-yl)propan-1-ol 
• 132631-08-4 methyl α,α,1-trimethyl-1H-indole-3-acetate 
• 72228-40-1 (±)-methyl 2-(1-methyl-1H-indol-3-yl)propanoate 
• 406500-63-8 2-hydroxy-3-methyl-3-(1-methylindol-3-yl)butyronitrile 
• 2179-92-2 tri-n-butyltin cyanide 

Downstream Products

• 377779-93-6 N-[(1'R)-2'-hydroxy-1'-phenylethyl]-(2S)-2-amino-3-methyl-3-(1-methylindol-3-yl)butyramide 

Relevant academic research and scientific papers

Asymmetric synthesis of the highly methylated tryptophan portion of the hemiasterlin tripeptides

(equation presented) The asymmetric synthesis of the methylated tryptophan portion of hemiasterlin peptides is described. The key reactions are a SnCl4-mediated ring opening of epoxynitriles or epoxysulfones by N-methylindole followed by an asy

The antibody-drug conjugate hemiasterlin derivatives and their pharmaceutically (by machine translation)

[Problem] to give one specific target cell cytotoxic, normal cells to the cytotoxic is suppressed, the antibody-drug conjugate medicine hemiasterlin derivatives. (2) Formula [a]:[In the formula, mAb antibody expressed, q is 1 - 8 represents an integer of, h are 1 - 5 represents an integer of, g is an alanine residue (Ala) to represent, g is 1 - 4 represents an integer of, Y is a single bond or a formula (Y-a 1) is represented by the group, Z is formula (Z-a 1), equation (Z-a 2), equation (Z-a 3), formula (Z-a 4), formula (Z-a 5), type (Z-a 6), formula (Za-a 1), equation (Za-in 2), equation (Za-a 3), formula (Za-a 4), formula (Za-a 5), type (Za d 6), formula (Za-a 7), type (Za-in 8), or a group represented by formula (Za-a 10) (Za-a 9) formula a] is expressed by, antibody-drug conjugate or its pharmaceutically acceptable salt containing a drug. [Drawing] no (by machine translation)

MEDICINE CONTAINING ANTIBODY DRUG CONJUGATE CONTAINING HEMIASTERLIN DERIVATIVE

PROBLEM TO BE SOLVED: To provide medicines containing an antibody drug conjugate containing a hemiasterlin derivative, in which specific cytotoxicity to target cells is given, while cytotoxicity to normal cells is suppressed. SOLUTION: Provided is a medicine represented by formula (2-1), and containing an antibody drug conjugate or a pharmaceutically acceptable salt thereof [where, mAb represents an antibody, q represents an integer from 1 to 8, b represents an integer from 1 to 5, Z is a group represented by formula (Z-1), formula (Z-2), formula (Z-3), formula (Za-1), formula (Za-2), formula (Za-3), formula (Za-4), or formula (Za-5)]. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

A total synthesis of (-)-hemiasterlin using N-Bts methodology

A total synthesis of (-)-hemiasterlin has been accomplished in nine steps from 258 (>35% yield overall). An improved enantiocontrolled route to the tetramethyltryptophan subunit 32 was developed using an asymmetric Strecker synthesis (five steps, 50% yield from 25), and the dipeptide 22 was prepared in seven steps, 37% yield from valinol. The synthesis exploits the high reactivity of a Bts-protected amino acid chloride in the difficult peptide coupling of sterically hindered amino acid residues 18 and 20 to form 21 (70%, recrystallized) and also uses N-Bts intermediates for the high-yielding N-methylations of 14 and 31. In addition, the Bts-protected di-tert-butyl N-acylimidodicarbonate 33 is shown to undergo efficient coupling with 22 to form 34 (97% in the coupling step; 79% over the activation; coupling sequence from 32).