(-)-(3S,4aS,8aS,2'R,3'R) acetic acid 3-[3'-(3-tert-butylcarbamoyl-decahydro-isoquinolin-2-yl)-2'-hydroxy-1'-(thiophen-2-yl)-propylcarbamoyl]-2-methyl-phenyl ester

Base Information

• Chemical Name: (-)-(3S,4aS,8aS,2'R,3'R) acetic acid 3-[3'-(3-tert-butylcarbamoyl-decahydro-isoquinolin-2-yl)-2'-hydroxy-1'-(thiophen-2-yl)-propylcarbamoyl]-2-methyl-phenyl ester
• CAS No.: 690223-69-9
• Molecular Formula: C₃₁H₄₃N₃O₅S
• Molecular Weight: 569.766
• Mol file: 690223-69-9.mol

Synonyms:(-)-(3S,4aS,8aS,2'R,3'R) acetic acid 3-[3'-(3-tert-butylcarbamoyl-decahydro-isoquinolin-2-yl)-2'-hydroxy-1'-(thiophen-2-yl)-propylcarbamoyl]-2-methyl-phenyl ester

Chemical Property of (-)-(3S,4aS,8aS,2'R,3'R) acetic acid 3-[3'-(3-tert-butylcarbamoyl-decahydro-isoquinolin-2-yl)-2'-hydroxy-1'-(thiophen-2-yl)-propylcarbamoyl]-2-methyl-phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(3S,4aS,8aS,2'R,3'R) acetic acid 3-[3'-(3-tert-butylcarbamoyl-decahydro-isoquinolin-2-yl)-2'-hydroxy-1'-(thiophen-2-yl)-propylcarbamoyl]-2-methyl-phenyl ester

There total 9 articles about (-)-(3S,4aS,8aS,2'R,3'R) acetic acid 3-[3'-(3-tert-butylcarbamoyl-decahydro-isoquinolin-2-yl)-2'-hydroxy-1'-(thiophen-2-yl)-propylcarbamoyl]-2-methyl-phenyl ester 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: 66.0%

3-acetoxy-2-methylbenzoic acid (168899-58-9) + (-)-(3S,4aS,8aS,2'R,3'R)-[3'-amino-2'-hydroxy-3'-(thiophen-2-yl)-propyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide (690223-68-8) → (-)-(3S,4aS,8aS,2'R,3'R) acetic acid 3-[3'-(3-tert-butylcarbamoyl-decahydro-isoquinolin-2-yl)-2'-hydroxy-1'-(thiophen-2-yl)-propylcarbamoyl]-2-methyl-phenyl ester (690223-69-9)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2004.02.026

Reference yield:

ethyl (E)-3-(thiophen-2-yl)acrylate (13979-15-2,70326-81-7) → (-)-(3S,4aS,8aS,2'R,3'R) acetic acid 3-[3'-(3-tert-butylcarbamoyl-decahydro-isoquinolin-2-yl)-2'-hydroxy-1'-(thiophen-2-yl)-propylcarbamoyl]-2-methyl-phenyl ester (690223-69-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 66 percent / AD mix-β; (DHQD)2PHAL; MeSO2NH2 / H2O; 2-methyl-propan-2-ol / 15 h / 0 - 15 °C

2: SOCl₂; pyridine / CH₂Cl₂ / 15 h / 0 °C

3: 17 mg / sodium azide / acetonitrile; dimethylformamide / 16 h / 15 °C

4: 90 percent / BH₃*SMe₂; NaBH₄ / tetrahydrofuran / 3 h / 20 °C

5: 80 percent / pyridine / CH₂Cl₂ / 24 h / 0 - 20 °C

6: K₂CO₃ / propan-2-ol / 21 h / 50 °C

7: 91 percent / hydrogen / Pd/C / methanol / 3 h / 20 °C

8: 62 percent / DMAP; DCC / CH₂Cl₂ / 2 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; thionyl chloride; sodium azide; methanesulfonamide; dimethylsulfide borane complex; hydrogen; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; tert-butyl alcohol;

DOI:10.1016/j.tet.2005.04.048

Reference yield:

(+)-(2R,3R)-3-azido-3-thiophen-2-yl-propane-1,2-diol (690223-65-5) → (-)-(3S,4aS,8aS,2'R,3'R) acetic acid 3-[3'-(3-tert-butylcarbamoyl-decahydro-isoquinolin-2-yl)-2'-hydroxy-1'-(thiophen-2-yl)-propylcarbamoyl]-2-methyl-phenyl ester (690223-69-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / pyridine / CH₂Cl₂ / 24 h / 0 - 20 °C

2: K₂CO₃ / propan-2-ol / 21 h / 50 °C

3: 91 percent / hydrogen / Pd/C / methanol / 3 h / 20 °C

4: 62 percent / DMAP; DCC / CH₂Cl₂ / 2 h / 20 °C

With pyridine; dmap; hydrogen; potassium carbonate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; dichloromethane; isopropyl alcohol;

DOI:10.1016/j.tet.2005.04.048

upstream raw materials:

3-acetoxy-2-methylbenzoic acid

(-)-(3S,4aS,8aS,2'R,3'R)-[3'-amino-2'-hydroxy-3'-(thiophen-2-yl)-propyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

(+)-(2R,3R)-toluene-4-sulfonic acid 3-azido-2-hydroxy-3-thiophen-2-yl-propyl ester

ethyl (E)-3-(thiophen-2-yl)acrylate