1,1-Dimethylethyl N-[(1S)-2-(dimethylphenylsilyl)-1-methyl-2-oxoethyl]carbamate

Base Information

• Chemical Name: 1,1-Dimethylethyl N-[(1S)-2-(dimethylphenylsilyl)-1-methyl-2-oxoethyl]carbamate
• CAS No.: 867325-88-0
• Molecular Formula: C₁₆H₂₅NO₃Si
• Molecular Weight: 307.465
• DSSTox Substance ID: DTXSID701136641
• Mol file: 867325-88-0.mol

Synonyms:DTXSID701136641;1,1-Dimethylethyl N-[(1S)-2-(dimethylphenylsilyl)-1-methyl-2-oxoethyl]carbamate;867325-88-0

Chemical Property of 1,1-Dimethylethyl N-[(1S)-2-(dimethylphenylsilyl)-1-methyl-2-oxoethyl]carbamate

Chemical Property:

• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 307.16037019
• Heavy Atom Count: 21
• Complexity: 382

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C(=O)[Si](C)(C)C1=CC=CC=C1)NC(=O)OC(C)(C)C
• Isomeric SMILES: C[C@@H](C(=O)[Si](C)(C)C1=CC=CC=C1)NC(=O)OC(C)(C)C

Technology Process of 1,1-Dimethylethyl N-[(1S)-2-(dimethylphenylsilyl)-1-methyl-2-oxoethyl]carbamate

There total 3 articles about 1,1-Dimethylethyl N-[(1S)-2-(dimethylphenylsilyl)-1-methyl-2-oxoethyl]carbamate 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: 72.0%

dimethyl(phenyl)silyllithium (3839-31-4) + (4S)-N-tert-Butyloxycarbonyl4-methyl-1,3-oxazolidin-5-one (172096-94-5) → [(1S)-2-(dimethylphenylsilanyl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester (867325-88-0)

Guidance literature:

In tetrahydrofuran; at -78 ℃;

DOI:10.1021/ol049826m

Reference yield: 48.0%

dimethyl(phenyl)silyllithium (3839-31-4) + [(1S)-2-imidazol-1-yl-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester (54430-64-7,86194-94-7,92008-48-5) → [(1S)-2-(dimethylphenylsilanyl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester (867325-88-0)

Guidance literature:

dimethyl(phenyl)silyllithium; With CuCN; In tetrahydrofuran; at 0 ℃; for 0.333333h;

[(1S)-2-imidazol-1-yl-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1039/b510756c

Reference yield:

L-N-Boc-Ala (15761-38-3) → [(1S)-2-(dimethylphenylsilanyl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester (867325-88-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 98 percent / tetrahydrofuran / 0.5 h / 0 °C

2.1: CuCN / tetrahydrofuran / 0.33 h / 0 °C

2.2: 48 percent / tetrahydrofuran / 0.5 h / -78 °C

With CuCN; In tetrahydrofuran;

DOI:10.1039/b510756c

upstream raw materials:

dimethyl(phenyl)silyllithium

(4S)-N-tert-Butyloxycarbonyl₄-methyl-1,3-oxazolidin-5-one

[(1S)-2-imidazol-1-yl-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester

L-N-Boc-Ala

Downstream raw materials:

benzyl-[(1S)-2-(dimethylphenylsilanyl)-1-methylallyl]-carbamic acid tert-butyl ester

{tert-butoxycarbonyl-[(1S)-2-(dimethylphenylsilanyl)-1-methylallyl]amino}-acetic acid methyl ester

[(1S)-2-(dimethylphenylsilanyl)-1-methylallylamino]-acetic acid methyl ester

(1S)-2-(dimethylphenylsilanyl)-1-methylallylamine