377779-88-9

Basic information

• Product Name: (2E,4S,2'S)-4-{[2'-[(benzothiazole-2-sulfonyl)amino]-3',3'-dimethylbutyryl]methylamino}-2,5-dimethylhex-2-enoic acid ethyl ester
• CAS NO: 377779-88-9
• Molecular Weight: 509.691
• Mol File: 377779-88-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2E,4S,2'S)-4-{[2'-[(benzothiazole-2-sulfonyl)amino]-3',3'-dimethylbutyryl]methylamino}-2,5-dimethylhex-2-enoic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2E,4S,2'S)-4-{[2'-[(benzothiazole-2-sulfonyl)amino]-3',3'-dimethylbutyryl]methylamino}-2,5-dimethylhex-2-enoic acid ethyl ester(377779-88-9)
• EPA Substance Registry System: (2E,4S,2'S)-4-{[2'-[(benzothiazole-2-sulfonyl)amino]-3',3'-dimethylbutyryl]methylamino}-2,5-dimethylhex-2-enoic acid ethyl ester(377779-88-9)

Safety Data

• Hazardous Substances Data: 377779-88-9(Hazardous Substances Data)

Upstream product

• 184434-18-2 (2E,4S)-4-methylamino-2,5-dimethylhex-2-enoic acid ethyl ester 
• 377779-87-8 (S)-2-(Benzothiazole-2-sulfonylamino)-3,3-dimethyl-butyryl chloride 

Relevant articles and documents

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).