(S)-methyl 2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxo-3-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)pyrrolidin-1-yl)-6-((tert-butoxycarbonyl)amino)hexanoate

Base Information

• Chemical Name: (S)-methyl 2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxo-3-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)pyrrolidin-1-yl)-6-((tert-butoxycarbonyl)amino)hexanoate
• CAS No.: 1422538-35-9
• Molecular Formula: C₄₂H₆₂N₄O₇Si
• Molecular Weight: 763.062
• Mol file: 1422538-35-9.mol

Synonyms:(S)-methyl 2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxo-3-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)pyrrolidin-1-yl)-6-((tert-butoxycarbonyl)amino)hexanoate

Chemical Property of (S)-methyl 2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxo-3-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)pyrrolidin-1-yl)-6-((tert-butoxycarbonyl)amino)hexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-methyl 2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxo-3-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)pyrrolidin-1-yl)-6-((tert-butoxycarbonyl)amino)hexanoate

There total 9 articles about (S)-methyl 2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxo-3-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)pyrrolidin-1-yl)-6-((tert-butoxycarbonyl)amino)hexanoate 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: 71.0%

(2R,4S)-benzyl 2-tert-butyl-5-oxo-4-(2-oxoethyl)-4-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)oxazolidine-3-carboxylate (1422538-30-4) + N-ε-tert-butoxycarbonyl-L-lysine methyl ester hydrochloride (2389-48-2) → (S)-methyl 2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxo-3-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)pyrrolidin-1-yl)-6-((tert-butoxycarbonyl)amino)hexanoate (1422538-35-9)

Guidance literature:

(2R,4S)-benzyl 2-tert-butyl-5-oxo-4-(2-oxoethyl)-4-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)oxazolidine-3-carboxylate; N-ε-tert-butoxycarbonyl-L-lysine methyl ester hydrochloride; With sodium acetate; In methanol; for 1h; Molecular sieve; Inert atmosphere;

With sodium cyanoborohydride; In methanol; at 20 ℃; Inert atmosphere;

With benzotriazol-1-ol; In toluene; for 6h; Reflux; Inert atmosphere;

DOI:10.1021/jo302737j

Reference yield:

(R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(1-(triisopropylsilyl)-1H-indol-3-yl)propanoate (1422538-25-7) → (S)-methyl 2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxo-3-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)pyrrolidin-1-yl)-6-((tert-butoxycarbonyl)amino)hexanoate (1422538-35-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: stannic tetrachloride pentahydrate / ethyl acetate / 48 h / 0 - 20 °C / Inert atmosphere

2.1: lithium hydroxide / tetrahydrofuran; water / 4 h / 20 °C / Inert atmosphere

3.1: sodium hydroxide / water; ethanol / 1 h / 20 °C / Inert atmosphere

3.2: 12 h / Inert atmosphere; Molecular sieve; Reflux

4.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 1 h / -78 °C / Inert atmosphere

4.2: -78 - -30 °C / Inert atmosphere

5.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / 20 h / Inert atmosphere

6.1: sodium periodate / water / 24 h / 20 °C / Inert atmosphere

7.1: sodium acetate / methanol / 1 h / Molecular sieve; Inert atmosphere

7.2: 20 °C / Inert atmosphere

7.3: 6 h / Reflux; Inert atmosphere

With sodium periodate; osmium(VIII) oxide; stannic tetrachloride pentahydrate; sodium acetate; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; methanol; ethanol; water; ethyl acetate; acetone; toluene;

DOI:10.1021/jo302737j

Reference yield:

C36H52N2O6Si → (S)-methyl 2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxo-3-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)pyrrolidin-1-yl)-6-((tert-butoxycarbonyl)amino)hexanoate (1422538-35-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium periodate / water / 24 h / 20 °C / Inert atmosphere

2.1: sodium acetate / methanol / 1 h / Molecular sieve; Inert atmosphere

2.2: 20 °C / Inert atmosphere

2.3: 6 h / Reflux; Inert atmosphere

With sodium periodate; sodium acetate; In methanol; water;

DOI:10.1021/jo302737j

upstream raw materials:

(R)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid methyl ester

triisopropylsilyl chloride

(R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(1-(triisopropylsilyl)-1H-indol-3-yl)propanoate

(R)-methyl 2-amino-3-(1-(triisopropylsilyl)-1H-indol-3-yl)propanoate

Downstream raw materials:

C₃₇H₄₈N₆O₆

C₄₆H₅₇N₇O₇