144370-38-7

Basic information

• Product Name: thiangazole
• Synonyms: thiangazole
• CAS NO: 144370-38-7
• Molecular Formula: C26H29N5O2S3
• Molecular Weight: 539.73576
• Mol File: 144370-38-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.38g/cm³
• Refractive Index: 1.701
• PKA: 14.11±0.46(Predicted)
• CAS DataBase Reference: thiangazole(CAS DataBase Reference)
• NIST Chemistry Reference: thiangazole(144370-38-7)
• EPA Substance Registry System: thiangazole(144370-38-7)

Safety Data

• Hazardous Substances Data: 144370-38-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C26H29N5O2S3/c1-16-19(20(32)27-5)28-21(33-16)24(2)13-35-23(30-24)26(4)15-36-22(31-26)25(3)14-34-18(29-25)12-11-17-9-7-6-8-10-17/h6-12H,13-15H2,1-5H3,(H,27,32)/b12-11+

Upstream product

• 1100-88-5 benzyltriphenylphosphonium chloride 
• 257278-51-6 2-((4R,4'S,4''S)-2''-Formyl-4,4',4''-trimethyl-4,5,4',5',4'',5''-hexahydro-[2,4';2',4'']terthiazol-4-yl)-5-methyl-oxazole-4-carboxylic acid methylamide 
• 157770-64-4 (4S)-4-methyl-4-<2'(4'R)-4'-methoxycarbonyl-4'-methyl-Δ²-thiazoline>-2-cinnamyl-Δ²-thiazoline 
• 165054-77-3 (4S)-4-methyl-4-<2'(4'S)-4'-carboxamide-4'-methyl-Δ²-thiazoline>-2-cinnamyl-Δ²-thiazoline 
• 157770-59-7 (4S)-4-methyl-4-<2'(4'R)-4'-nitrile-4'-methyl-Δ²-thiazoline>-2-cinnamyl-Δ²-thiazoline 
• 157770-62-2 (4R)-4-methyl-4-carboxamide-2-cinnamyl-Δ²-thiazoline 
• 157770-61-1 (4R)-4-methoxycarbonyl-4-methyl-2-cinnamyl-Δ²-thiazoline 
• 157770-63-3 (4R)-4-methyl-4-nitrile-2-cinnamyl-Δ²-thiazoline 
• 4360-47-8 cinnamonitrile 
• 158785-74-1 (4R,4'S,4''S)-2''-(Diphenyl-phosphinoylmethyl)-4,4',4''-trimethyl-4,5,4',5',4'',5''-hexahydro-[2,4';2',4'']terthiazole-4-carboxylic acid ethyl ester 
• 257278-40-3 5-Methyl-2-[(4R,4'S,4''S)-4,4',4''-trimethyl-2''-((E)-styryl)-4,5,4',5',4'',5''-hexahydro-[2,4';2',4'']terthiazol-4-yl]-oxazole-4-carboxylic acid 
• 158785-73-0 (4R,4'S)-2'-(Diphenyl-phosphinoylmethyl)-4,4'-dimethyl-4,5,4',5'-tetrahydro-[2,4']bithiazolyl-4-carboxylic acid ethyl ester 
• 158785-75-2 (4R,4'S,4''S)-4,4',4''-Trimethyl-2''-((E)-styryl)-4,5,4',5',4'',5''-hexahydro-[2,4';2',4'']terthiazole-4-carboxylic acid ethyl ester 
• 158785-76-3 (4R,4'S,4''S)-4,4',4''-Trimethyl-2''-((E)-styryl)-4,5,4',5',4'',5''-hexahydro-[2,4';2',4'']terthiazole-4-carboxylic acid amide 

Relevant articles and documents

Total synthesis of thiangazole

A method for total synthesis of thiangazole (1), a tris-thiazoline- oxazole metabolite, is described. The key intermediate 9, a linear tetrapeptide amide composed of three S-benzyl-2-methylcysteine residues and a O-benzyl-threonine amide, was synthesized in 4 steps using 2-chloro-1,3- dimethyl-imidazolidium hexafluorophosphate(CIP)mediated activation. The successive thiazoline/oxazole rings were constructed by TiCl4mediated cycledehydration followed by acid-catalyzed Robinson-Gabriel reaction without difficulty.

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, a novel naturally occurring HIV-1 inhibitor from Polyangium sp

The total synthesis of the cinnamyl-oxazole substituted tris-thiazoline containing metabolite (-)-thiangazole (1) is described. The synthesis is based on elaboration of the R-2-methylcysteine derived bis-thiazoline nitrile (5) and oxazole (6) intermediate