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

Base Information

• Chemical Name: methyl 6-[(3S,7R,7aR)-6-benzyl-5-oxo-3-phenyltetrahydro-5H-imidazo[1,5-c][1,3]thiazol-7-yl]-6-oxohexanoate
• CAS No.: 848302-21-6
• Molecular Formula: C₂₅H₂₈N₂O₄S
• Molecular Weight: 452.574
• Mol file: 848302-21-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

(3S,7aR)-6-benzyl-7-hydroxy-3-phenyltetrahydro-5H-imidazo[1,5-c][1,3]thiazol-5-one (848302-22-7) → methyl 6-[(3S,7R,7aR)-6-benzyl-5-oxo-3-phenyltetrahydro-5H-imidazo[1,5-c][1,3]thiazol-7-yl]-6-oxohexanoate (848302-21-6)

Guidance literature:

Multi-step reaction with 3 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

3: 0.630 g / diethyl ether / 0.17 h

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

DOI:10.1021/jo0488107

Reference yield:

(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) → methyl 6-[(3S,7R,7aR)-6-benzyl-5-oxo-3-phenyltetrahydro-5H-imidazo[1,5-c][1,3]thiazol-7-yl]-6-oxohexanoate (848302-21-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / KOH; tert-butyl hydrogen peroxide / H₂O; methanol / 0.5 h

2: 0.630 g / diethyl ether / 0.17 h

With tert.-butylhydroperoxide; potassium hydroxide; In methanol; diethyl ether; water; 1: Baeyer-Villiger oxidation;

DOI:10.1021/jo0488107

Reference yield:

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) + diazomethane (186581-53-3,908094-01-9,334-88-3) → methyl 6-[(3S,7R,7aR)-6-benzyl-5-oxo-3-phenyltetrahydro-5H-imidazo[1,5-c][1,3]thiazol-7-yl]-6-oxohexanoate (848302-21-6)

Guidance literature:

In diethyl ether; for 0.166667h;

DOI:10.1021/jo0488107

upstream raw materials:

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

diazomethane

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

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

Downstream raw materials:

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

biotin

N,N'-dibenzylbiotin methyl ester