Thiangazole

Base Information

• Chemical Name: Thiangazole
• CAS No.: 138667-71-7
• Molecular Formula: C26H29N5O2S3
• Molecular Weight: 539.747
• Nikkaji Number: J609.581J
• Wikidata: Q105117333
• Metabolomics Workbench ID: 98679
• Mol file: 138667-71-7.mol

Synonyms:thiangazole;thiangazole, (4R-(2(2'(2''(E),4''S*),4'S*),4R*))-isomer

Chemical Property of Thiangazole

Chemical Property:

• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 539.14833871
• Heavy Atom Count: 36
• Complexity: 1010

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(N=C(O1)C2(CSC(=N2)C3(CSC(=N3)C4(CSC(=N4)C=CC5=CC=CC=C5)C)C)C)C(=O)NC
• Isomeric SMILES: CC1=C(N=C(O1)[C@@]2(CSC(=N2)[C@@]3(CSC(=N3)[C@@]4(CSC(=N4)/C=C/C5=CC=CC=C5)C)C)C)C(=O)NC

Technology Process of Thiangazole

There total 29 articles about Thiangazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

(4R,4'S,4''S)-5-Methyl-2-<4,4',4''-trimethyl-2''-phenethyl-4,5,4',5',4'',5''-hexahydro<2,4':2',4''>terthiazol-4-yl>oxazole-4-carboxylic acid methylamine (158395-19-8) → (-)-Thiangazole (138667-71-7,144370-38-7)

Guidance literature:

With benzeneseleninic acid; In benzene; at 60 ℃; for 0.75h;

DOI:10.1021/jo00127a030

Reference yield: 75.0%

(4S)-4-methyl-4'<2'(4'S)-4'-methyl-4'(2''-(4''R)-4''-methyl-4''-(2'''-(4'''-methoxycarbonyl-5'''-methyl)oxazole)-Δ2-thiazoline)-Δ2-thiazoline>-2-cinnamyl-Δ2-thiazoline (157770-69-9) → (-)-Thiangazole (138667-71-7,144370-38-7)

Guidance literature:

With methylamine; In ethanol; at 25 ℃;

DOI:10.1016/S0040-4039(00)77284-4

Reference yield: 64.0%

benzyltriphenylphosphonium chloride (1100-88-5) + 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 (257278-51-6) → (-)-Thiangazole (138667-71-7,144370-38-7) + (21Z)-thiangazole (144370-38-7)

Guidance literature:

With sodium hydroxide; In dichloromethane; water; at 20 ℃; for 0.5h;

DOI:10.1002/(SICI)1099-0690(199912)1999:12<3381::AID-EJOC3381>3.0.CO;2-W

upstream raw materials:

(4S)-4-methyl-4'<2'(4'S)-4'-methyl-4'(2''-(4''R)-4''-methyl-4''-(2'''-(4'''-methoxycarbonyl-5'''-methyl)oxazole)-Δ²-thiazoline)-Δ²-thiazoline>-2-cinnamyl-Δ²-thiazoline

(4R,4'S,4''S)-5-Methyl-2-<4,4',4''-trimethyl-2''-phenethyl-4,5,4',5',4'',5''-hexahydro<2,4':2',4''>terthiazol-4-yl>oxazole-4-carboxylic acid methylamine

methylamine

benzyltriphenylphosphonium chloride

Downstream raw materials:

(4R,4'S,4''S)-5-Methyl-2-<4,4',4''-trimethyl-2''-phenethyl-4,5,4',5',4'',5''-hexahydro<2,4':2',4''>terthiazol-4-yl>oxazole-4-carboxylic acid methylamine

5-Hydroxymethyl-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 methylamide

5-Methyl-2-((4R,4'S,4''S)-4,4',4''-trimethyl-4,5,4',5',4'',5''-hexahydro-[2,4';2',4'']terthiazol-4-yl)-oxazole-4-carboxylic acid methylamide

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