819081-96-4

Basic information

• Product Name: 2-((S)-2-Hydroxy-1-{(S)-3-hydroxy-2-[(S)-3-hydroxy-2-methyl-2-(3-phenyl-propionylamino)-propionylamino]-2-methyl-propionylamino}-1-methyl-ethyl)-5-methyl-oxazole-4-carboxylic acid methylamide
• Synonyms: 2-((S)-2-Hydroxy-1-{(S)-3-hydroxy-2-[(S)-3-hydroxy-2-methyl-2-(3-phenyl-propionylamino)-propionylamino]-2-methyl-propionylamino}-1-methyl-ethyl)-5-methyl-oxazole-4-carboxylic acid methylamide
• CAS NO: 819081-96-4
• Molecular Weight: 547.608
• Mol File: 819081-96-4.mol

Chemical Properties

• CAS DataBase Reference: 2-((S)-2-Hydroxy-1-{(S)-3-hydroxy-2-[(S)-3-hydroxy-2-methyl-2-(3-phenyl-propionylamino)-propionylamino]-2-methyl-propionylamino}-1-methyl-ethyl)-5-methyl-oxazole-4-carboxylic acid methylamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-((S)-2-Hydroxy-1-{(S)-3-hydroxy-2-[(S)-3-hydroxy-2-methyl-2-(3-phenyl-propionylamino)-propionylamino]-2-methyl-propionylamino}-1-methyl-ethyl)-5-methyl-oxazole-4-carboxylic acid methylamide(819081-96-4)
• EPA Substance Registry System: 2-((S)-2-Hydroxy-1-{(S)-3-hydroxy-2-[(S)-3-hydroxy-2-methyl-2-(3-phenyl-propionylamino)-propionylamino]-2-methyl-propionylamino}-1-methyl-ethyl)-5-methyl-oxazole-4-carboxylic acid methylamide(819081-96-4)

Safety Data

• Hazardous Substances Data: 819081-96-4(Hazardous Substances Data)

Upstream product

• 171011-98-6 (R)-2-[(S)-3-Benzyloxy-2-methyl-2-(2-trimethylsilanyl-ethanesulfonylamino)-propionylamino]-3-oxo-butyric acid methyl ester 
• 171011-88-4 2-<(1S)-2-(Benzyloxy)-1-<<(2S)-3-(benzyloxy)-2-<<(3S)-(benzyloxy)-2-methyl-2-<<<2-(trimethylsilyl)ethyl>sulfonyl>amino>propionyl>amino>-2-methyl-propionyl>amino>-1-methylethyl>-5-methyloxazole-4-carboxylic acid methylamide 
• 819081-93-1 2-{(S)-1-[(S)-2-((S)-2-Amino-3-benzyloxy-2-methyl-propionylamino)-3-benzyloxy-2-methyl-propionylamino]-2-benzyloxy-1-methyl-ethyl}-5-methyl-oxazole-4-carboxylic acid methylamide 
• 171011-86-2 2-<(1S)-2-(Benzyloxy)-1-methyl-1-<<<2-(trimethylsilyl)ethyl>sulfonyl>amino>ethyl>-5-methyloxazole-4-carboxylic acid methyl ester 
• 171011-99-7 2-<(1S)-2-(Benzyloxy)-1-methyl-1-<<<2-(trimethylsilyl)ethyl>sulfonyl>amino>ethyl>-5-methyloxazole-4-carboxylic acid methylamide 
• 171011-87-3 2-<(1S)-2-(Benzyloxy)-1-<<(2S)-3-(benzyloxy)-2-methyl-2-<<<2-(trimethylsilyl)ethyl>sulfonyl>amino>propionyl>amino>-1-methylethyl>-5-methyloxazole-4-carboxylic acid methylamide 
• 819081-59-9 2-[(S)-1-((S)-2-Amino-3-benzyloxy-2-methyl-propionylamino)-2-benzyloxy-1-methyl-ethyl]-5-methyl-oxazole-4-carboxylic acid methylamide 
• 168553-66-0 (2R,3S)-2-[(S)-3-Benzyloxy-2-methyl-2-(2-trimethylsilanyl-ethanesulfonylamino)-propionylamino]-3-hydroxy-butyric acid methyl ester 
• 819081-56-6 2-((S)-1-Amino-2-benzyloxy-1-methyl-ethyl)-5-methyl-oxazole-4-carboxylic acid methylamide 
• 171011-89-5 2-<(1S)-2-(Benzyloxy)-1-<<(2S)-3-(benzyloxy)-2-<<(3S)-3-(benzyloxy)-2-methyl-2-<(3-phenylpropionyl)amino>propionyl>amino>-2-methylpropionyl>amino>-1-methylethyl>-5-methyloxazole-4-carboxylic acid methylamide 

Downstream Products

• 171011-90-8 (4'S,4''S,4'''S)-5,4',4'',4''-Tetramethyl-2'''-phenethyl-4',5',4'',5'',4''',5'''-hexahydro<2,4':2',4'':2'',4'''>quateroxazole-4-carboxylic acid methylamine 

Relevant articles and documents

From Aziridines to Oxazolines and Thiazolines: The Heterocyclic Route to Thiangazole

Since its isolation in 1991, the polyazole natural product thiangazole has become a popular target for total synthesis due to its challenging array of heterocyclic segments and its reported potent antiviral activity. The synthetic activity toward thiangazole is reviewed and a novel approach that takes advantage of aziridine and oxazoline intermediates en route to thiazolines is presented.

Total Synthesis of (-)-Thiangazole and Structurally Related Polyazoles

Thiangazole was reported to be an extremely potent, nontoxic inhibitor of HIV-1 in MT4 cell assays.By employing a strategy of selective oxazoline-thiazoline interconversions, we have accomplished a total synthesis of the natural product in 16 steps and 1.1percent overall yield from (S)-α-methylserine.This new methodology is especially useful for the preparation of analogs of thiangazole and structure-activity studies.Our preliminary biological testing of (-)-thiangazole revealed a high level of cytotoxicity that was considerably reduced in the oxazoline-containing analogs.