(S)-2-(Benzyloxycarbonyl-methyl-amino)-4-methyl-pentanoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxycarbonyl)-ethyl ester

Base Information

• Chemical Name: (S)-2-(Benzyloxycarbonyl-methyl-amino)-4-methyl-pentanoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxycarbonyl)-ethyl ester
• CAS No.: 220657-12-5
• Molecular Formula: C₃₀H₅₀N₂O₉Si
• Molecular Weight: 610.82
• Mol file: 220657-12-5.mol

Synonyms:(S)-2-(Benzyloxycarbonyl-methyl-amino)-4-methyl-pentanoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxycarbonyl)-ethyl ester

Chemical Property of (S)-2-(Benzyloxycarbonyl-methyl-amino)-4-methyl-pentanoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxycarbonyl)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-(Benzyloxycarbonyl-methyl-amino)-4-methyl-pentanoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxycarbonyl)-ethyl ester

There total 2 articles about (S)-2-(Benzyloxycarbonyl-methyl-amino)-4-methyl-pentanoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxycarbonyl)-ethyl 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: 86.0%

N-benzyloxycarbonyl-N-methyl-L-leucine (33099-08-0) + Boc-threonine [(2-trimethylsilyl)ethoxy]methyl ester (126587-71-1) → (S)-2-(Benzyloxycarbonyl-methyl-amino)-4-methyl-pentanoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxycarbonyl)-ethyl ester (220657-12-5)

Guidance literature:

With dmap; Isopropenyl chloroformate; triethylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/S0040-4020(98)01042-4

Reference yield:

Z-Leu-OH (2018-66-8) → (S)-2-(Benzyloxycarbonyl-methyl-amino)-4-methyl-pentanoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxycarbonyl)-ethyl ester (220657-12-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / KOH, nBu₄NHSO₄ / tetrahydrofuran / 0.5 h / Ambient temperature

2: 86 percent / Et₃N, DMAP, isopropenyl chloroformate / CH₂Cl₂ / 1 h / 0 °C

With dmap; potassium hydroxide; Isopropenyl chloroformate; tetra(n-butyl)ammonium hydrogensulfate; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(98)01042-4

Reference yield:

(S)-2-(Benzyloxycarbonyl-methyl-amino)-4-methyl-pentanoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxycarbonyl)-ethyl ester (220657-12-5) → (S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-methyl-amino}-4-methyl-pentanoic acid (1R,2S)-2-tert-butoxycarbonylamino-2-carboxy-1-methyl-ethyl ester (185610-65-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / H₂ / Pd/C / methanol; ethyl acetate / 3 h / 2068.59 Torr

2: 1.) BOP-Cl, NMM, 2.) NMM / 1.) CH₂Cl₂, -15 deg C, 0.5 h, 2.) 0 deg C, 6 h

3: MgBr₂*Et₂O / CH₂Cl₂ / 1.) -20 deg C, 1 h, 2.) 0 deg C, 3.5 h

With 4-methyl-morpholine; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; magnesium bromide; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4020(98)01042-4

upstream raw materials:

N-benzyloxycarbonyl-N-methyl-L-leucine

Boc-threonine [(2-trimethylsilyl)ethoxy]methyl ester

Z-Leu-OH

Downstream raw materials:

N--L-leucyl>-L-prolyl>-N-methyl-L-leucine ester with (3S,4R,5S)-3-<(triisopropylsilyl)oxy>-4-<(2S,3R)-2-<(tert-butoxycarbonyl)amino>-3-hydroxybutyramido>-5-methylheptanoic acid, (1S,2S,3S)-1-isopropyl-2-(methoxymethoxy)-3-...

(S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-methyl-amino}-4-methyl-pentanoic acid (1R,2S)-2-tert-butoxycarbonylamino-2-carboxy-1-methyl-ethyl ester

(S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-methyl-amino}-4-methyl-pentanoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxycarbonyl)-ethyl ester

N--L-leucyl>-L-prolyl>-N-methyl-L-leucine ester with (3S,4R,5S)-3-<(triisopropylsilyl)oxy>-4-<(2S,3R)-2-<(tert-butoxycarbonyl)amino>-3-hydroxybutyramido>-5-methylheptanoic acid, (1S,2S,3R)-4-hydroxy-1-isopropyl-2-(methoxy...