6-[(3S,7R,7aR)-6-benzyl-5-oxo-3-phenyltetrahydro-1H-imidazo[1,5-c][1,3]thiazol-7-yl]-6-oxohexanoic acid

Base Information

• Chemical Name: 6-[(3S,7R,7aR)-6-benzyl-5-oxo-3-phenyltetrahydro-1H-imidazo[1,5-c][1,3]thiazol-7-yl]-6-oxohexanoic acid
• CAS No.: 112878-96-3
• Molecular Formula: C₂₄H₂₆N₂O₄S
• Molecular Weight: 438.547
• Mol file: 112878-96-3.mol

Synonyms:6-[(3S,7R,7aR)-6-benzyl-5-oxo-3-phenyltetrahydro-1H-imidazo[1,5-c][1,3]thiazol-7-yl]-6-oxohexanoic acid

Chemical Property of 6-[(3S,7R,7aR)-6-benzyl-5-oxo-3-phenyltetrahydro-1H-imidazo[1,5-c][1,3]thiazol-7-yl]-6-oxohexanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-[(3S,7R,7aR)-6-benzyl-5-oxo-3-phenyltetrahydro-1H-imidazo[1,5-c][1,3]thiazol-7-yl]-6-oxohexanoic acid

There total 3 articles about 6-[(3S,7R,7aR)-6-benzyl-5-oxo-3-phenyltetrahydro-1H-imidazo[1,5-c][1,3]thiazol-7-yl]-6-oxohexanoic acid 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: 79.9%

(3S,7R,7aR)-6-benzyl-7-(2-oxocyclohexyl)-3-phenyltetrahydro-5H-imidazo[1,5-c][1,3]thiazol-5-one → 6-[(3S,7R,7aR)-6-benzyl-5-oxo-3-phenyltetrahydro-1H-imidazo[1,5-c][1,3]thiazol-7-yl]-6-oxohexanoic acid (112878-96-3)

Guidance literature:

With iron(III) chloride; oxygen; dimethyl sulfoxide; In methanol; at 55 ℃; for 12h; Temperature; Reagent/catalyst; Catalytic behavior;

Reference yield: 70.0%

(3S,7R,7aR)-6-benzyl-7-(1-hydroxy-2-oxocyclohexyl)-3-phenyl-tetrahydro-5H-imidazo[1,5-c][1,3]thiazol-5-one (848302-18-1) → 6-[(3S,7R,7aR)-6-benzyl-5-oxo-3-phenyltetrahydro-1H-imidazo[1,5-c][1,3]thiazol-7-yl]-6-oxohexanoic acid (112878-96-3)

Guidance literature:

With tert.-butylhydroperoxide; potassium hydroxide; In methanol; water; for 0.5h;

DOI:10.1021/jo0488107

Reference yield:

(3S,7aR)-6-benzyl-7-hydroxy-3-phenyltetrahydro-5H-imidazo[1,5-c][1,3]thiazol-5-one (848302-22-7) → 6-[(3S,7R,7aR)-6-benzyl-5-oxo-3-phenyltetrahydro-1H-imidazo[1,5-c][1,3]thiazol-7-yl]-6-oxohexanoic acid (112878-96-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / BF₃*Et₂O / CH₂Cl₂ / 0.17 h / 0 °C

2: 70 percent / KOH; tert-butyl hydrogen peroxide / H₂O; methanol / 0.5 h

With tert.-butylhydroperoxide; potassium hydroxide; boron trifluoride diethyl etherate; In methanol; dichloromethane; water; 2: Baeyer-Villiger oxidation;

DOI:10.1021/jo0488107

upstream raw materials:

(3S,7R,7aR)-6-benzyl-7-(1-hydroxy-2-oxocyclohexyl)-3-phenyl-tetrahydro-5H-imidazo[1,5-c][1,3]thiazol-5-one

(3S,7aR)-6-benzyl-7-hydroxy-3-phenyltetrahydro-5H-imidazo[1,5-c][1,3]thiazol-5-one

Downstream raw materials:

N,N'-dibenzylbiotin methyl ester

biotin

methyl (5Z)-5-[(3aS,6aR)-1,3-dibenzyl-2-oxohexahydro-4H-thieno[3,4-d]imidazol-4-ylidene]pentanoate