(1R,2S)-methyl 1-((1R,2R,5R)-5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxamido)-2-vinylcyclopropanecarboxylate

Base Information

• Chemical Name: (1R,2S)-methyl 1-((1R,2R,5R)-5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxamido)-2-vinylcyclopropanecarboxylate
• CAS No.: 1265883-91-7
• Molecular Formula: C₃₈H₅₂N₂O₅Si
• Molecular Weight: 644.927
• Mol file: 1265883-91-7.mol

Synonyms:(1R,2S)-methyl 1-((1R,2R,5R)-5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxamido)-2-vinylcyclopropanecarboxylate

Chemical Property of (1R,2S)-methyl 1-((1R,2R,5R)-5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxamido)-2-vinylcyclopropanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S)-methyl 1-((1R,2R,5R)-5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxamido)-2-vinylcyclopropanecarboxylate

There total 8 articles about (1R,2S)-methyl 1-((1R,2R,5R)-5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxamido)-2-vinylcyclopropanecarboxylate 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: 76.0%

(1R,2R,4R)-5-(tert-butyldiphenylsilanyloxy)-2-(hex-5-enyl-methylcarbamoyl)cyclohexanecarboxylic acid (1265883-90-6) + (1R,2S)-1-amino-2-vinyl-cyclopropyl carboxylic acid methyl ester (681260-04-8) → (1R,2S)-methyl 1-((1R,2R,5R)-5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxamido)-2-vinylcyclopropanecarboxylate (1265883-91-7)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; Inert atmosphere;

Reference yield: 76.0%

→ (1R,2S)-methyl 1-((1R,2R,5R)-5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxamido)-2-vinylcyclopropanecarboxylate (1265883-91-7)

Guidance literature:

Reference yield:

(1R,2R,4R,5S)-4-iodo-7-oxo-6-oxabicyclo[3.2.1]-octane-2-carboxylic acid methyl ester (1265882-88-9) → (1R,2S)-methyl 1-((1R,2R,5R)-5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxamido)-2-vinylcyclopropanecarboxylate (1265883-91-7)

Guidance literature:

Multi-step reaction with 9 steps

1: tris-(trimethylsilyl)silane; 1,1′-azobis(cyclohexanecarbonitrile) / toluene / 1.5 h / 90 °C

2: potassium carbonate / N,N-dimethyl-formamide / 16 h / Inert atmosphere

3: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

4: palladium 10% on activated carbon; hydrogen / ethanol / 16 h

5: toluene / 1.5 h / 110 °C

6: lithium hydroxide / tetrahydrofuran; water / 16 h / 20 °C

7: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

8: trifluoroacetic acid / dichloromethane / 16 h / 20 °C

9: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; tris-(trimethylsilyl)silane; palladium 10% on activated carbon; 1,1′-azobis(cyclohexanecarbonitrile); hydrogen; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

upstream raw materials:

(1R,2R,4R,5S)-4-iodo-7-oxo-6-oxabicyclo[3.2.1]-octane-2-carboxylic acid methyl ester

(1R,2R,5R)-7-oxo-6-oxabicyclo[3,2,1]octane-2-carboxylic acid methyl ester

(1R,2R,4R)-4-hydroxy-cyclohexane-1,2-dicarboxylic acid 2-benzyl ester 1-methyl ester

(1R,6S)-6-methoxycarbonyl-3-cyclohexene-1-carboxylic acid

Refernces

• 1、 -. "MACROCYCLIC SERINE PROTEASE INHIBITORS USEFUL AGAINST VIRAL INFECTIONS, PARTICULARLY HCV". Page/Page column 206. . Retrieved 2011/02/24.