(2S,3aR,5S,6S,7aS)-1-{(2S,3R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-3-chloro-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3aR,5S,6S,7aS)-1-{(2S,3R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-3-chloro-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid methyl ester
• CAS No.: 910230-92-1
• Molecular Formula: C₄₀H₅₉ClN₂O₁₀Si
• Molecular Weight: 791.454
• Mol file: 910230-92-1.mol

Synonyms:(2S,3aR,5S,6S,7aS)-1-{(2S,3R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-3-chloro-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid methyl ester

Chemical Property of (2S,3aR,5S,6S,7aS)-1-{(2S,3R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-3-chloro-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3aR,5S,6S,7aS)-1-{(2S,3R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-3-chloro-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid methyl ester

There total 3 articles about (2S,3aR,5S,6S,7aS)-1-{(2S,3R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-3-chloro-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid methyl 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: 57.0%

(2S,3R,2'R)-2-[3'-(tert-butyldiphenylsilyloxy)-2'-methoxypropionylamino]-3-chloro-4-methylpentanoic acid (910230-89-6) + methyl (2S,5S,6S,3aR,7aS)-5,6-bis(methoxymethoxy)octahydroindole-2-carboxylate (477351-62-5) → (2S,3aR,5S,6S,7aS)-1-{(2S,3R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-3-chloro-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid methyl ester (910230-92-1)

Guidance literature:

With 2,6-dimethylpyridine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In dichloromethane; at 0 ℃; for 4h;

DOI:10.1021/ja0625834

Reference yield:

(2R,1'S,2'R)-3-(tert-butyldiphenylsilyloxy)-N-(2'-chloro-1'-hydroxymethyl-3'-methylbutyl)-2-methoxypropionamide (910230-88-5) → (2S,3aR,5S,6S,7aS)-1-{(2S,3R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-3-chloro-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid methyl ester (910230-92-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 48 percent / 1,4-bis(diphenylphosphino)butane; diisopropylethylamine / Pd(OAc)2 / dimethylsulfoxide / 4 h / 100 °C

2.1: 95 percent / BBr₃ / CH₂Cl₂ / 48 h / 20 °C

3.1: K₂CO₃ / dimethylformamide / 0.5 h / 20 °C

3.2: 87 percent / dimethylformamide / 50 °C

With boron tribromide; potassium carbonate; N-ethyl-N,N-diisopropylamine; 1,4-di(diphenylphosphino)-butane; palladium diacetate; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1002/adsc.200606143

Reference yield:

(R)-3-(tert-butyldiphenylsilyloxy)-2-methoxypropionic acid (477351-74-9) → (2S,3aR,5S,6S,7aS)-1-{(2S,3R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-3-chloro-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid methyl ester (910230-92-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 0.56 g / 2,6-lutidine; PyBOP / CH₂Cl₂ / 18 h / 20 °C

2: 78 percent / CrO₃; H₅IO₆; H₂O / acetonitrile / 0.5 h / 0 °C

3: 57 percent / DEPBT; 2,6-lutidine / CH₂Cl₂ / 4 h / 0 °C

With 2,6-dimethylpyridine; chromium(VI) oxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; water; periodic acid; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In dichloromethane; acetonitrile;

DOI:10.1021/ja0625834

upstream raw materials:

(2S,3R,2'R)-2-[3'-(tert-butyldiphenylsilyloxy)-2'-methoxypropionylamino]-3-chloro-4-methylpentanoic acid

methyl (2S,5S,6S,3aR,7aS)-5,6-bis(methoxymethoxy)octahydroindole-2-carboxylate

(2R,1'S,2'R)-3-(tert-butyldiphenylsilyloxy)-N-(2'-chloro-1'-hydroxymethyl-3'-methylbutyl)-2-methoxypropionamide

(R)-3-(tert-butyldiphenylsilyloxy)-2-methoxypropionic acid

Downstream raw materials:

C₅₆H₈₅ClN₆O₁₃Si

(2S,3aR,5S,6S,7aS)-1-{(2S,3R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-3-chloro-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid