N-<(benzyloxy)carbonyl>-N-methyl-D-leucine 2-(trimethylsilyl)ethyl ester

Base Information

• Chemical Name: N-<(benzyloxy)carbonyl>-N-methyl-D-leucine 2-(trimethylsilyl)ethyl ester
• CAS No.: 129919-93-3
• Molecular Formula: C₂₀H₃₃NO₄Si
• Molecular Weight: 379.572

Synonyms:N-<(benzyloxy)carbonyl>-N-methyl-D-leucine 2-(trimethylsilyl)ethyl ester

Chemical Property of N-<(benzyloxy)carbonyl>-N-methyl-D-leucine 2-(trimethylsilyl)ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of N-<(benzyloxy)carbonyl>-N-methyl-D-leucine 2-(trimethylsilyl)ethyl ester

There total 2 articles about N-<(benzyloxy)carbonyl>-N-methyl-D-leucine 2-(trimethylsilyl)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%

2-(Trimethylsilyl)ethanol (2916-68-9) + N-methyl-N-(benzyloxycarbonyl)-D-leucine (65635-85-0) → N-<(benzyloxy)carbonyl>-N-methyl-D-leucine 2-(trimethylsilyl)ethyl ester (129919-93-3)

Guidance literature:

With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In N,N-dimethyl-formamide; for 24h; Ambient temperature;

DOI:10.1021/ja00177a030

Reference yield:

Z-D-Leu-OH (28862-79-5) → N-<(benzyloxy)carbonyl>-N-methyl-D-leucine 2-(trimethylsilyl)ethyl ester (129919-93-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / KOH, Bu₄N(+)HSO₄(-) / tetrahydrofuran

2: 78 percent / Et₃N, DCC, DMAP / CH₂Cl₂ / 22 h / Ambient temperature

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

DOI:10.1021/jo00097a022

Reference yield:

N-<(benzyloxy)carbonyl>-N-methyl-D-leucine 2-(trimethylsilyl)ethyl ester (129919-93-3) → didemnin B (114607-50-0,128821-14-7,77327-05-0)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogen / 10percent Pd/C / methanol; ethyl acetate / 15 h / 1810.02 Torr

2: 1.) BOP-Cl, triethylamine / 1.) CH₂Cl₂, -15 deg C, 30 min, 2.) 0 deg C,

3: tetrabutylammonium fluoride / dimethylformamide; tetrahydrofuran

4: 1.) BOP, N-methylmorpholine / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) RT, 3 h

With 4-methyl-morpholine; tetrabutyl ammonium fluoride; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja00177a030

upstream raw materials:

2-(Trimethylsilyl)ethanol

N-methyl-N-(benzyloxycarbonyl)-D-leucine

Z-D-Leu-OH

Downstream raw materials:

Cyclo<(N-L-prolyl-N-methyl-D-leucyl)-O-<oxy>-3-oxo-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-N,O-dimethyl-L-tyrosyl>-L-threonyl>

C₆₂H₉₁N₇O₁₆

N-Cbz-3,4-didehydro-L-prolyl-N-methyl-D-leucine

(2S,4R)-2-[((R)-1-Carboxy-3-methyl-butyl)-methyl-carbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

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