Methyl 4-[(tert-butoxycarbonyl)amino]-5-{[tert-butyl(dimethyl)silyl]oxy}pentanoate

Base Information

• Chemical Name: Methyl 4-[(tert-butoxycarbonyl)amino]-5-{[tert-butyl(dimethyl)silyl]oxy}pentanoate
• CAS No.: 96014-55-0
• Molecular Formula: C₁₇H₃₅NO₅Si
• Molecular Weight: 361.554
• DSSTox Substance ID: DTXSID40538074
• Mol file: 96014-55-0.mol

Synonyms:96014-55-0;Methyl 4-[(tert-butoxycarbonyl)amino]-5-{[tert-butyl(dimethyl)silyl]oxy}pentanoate;(S)-Methyl4-(boc-amino)-5-tbdms-pentanoate;methyl 5-[tert-butyl(dimethyl)silyl]oxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate;SCHEMBL211091;DTXSID40538074

Chemical Property of Methyl 4-[(tert-butoxycarbonyl)amino]-5-{[tert-butyl(dimethyl)silyl]oxy}pentanoate

Chemical Property:

• Refractive Index: 1.447
• Boiling Point: 408.1 °C at 760 mmHg
• Flash Point: 200.6 °C
• PSA: 73.86000
• Density: 0.983g/cm³
• LogP: 4.24560
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 361.22844975
• Heavy Atom Count: 24
• Complexity: 424

Purity/Quality:

98%Min ^*data from raw suppliers

(S)-METHYL4-(BOC-AMINO)-5-TBDMS-PENTANOATE 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CCC(=O)OC)CO[Si](C)(C)C(C)(C)C

Technology Process of Methyl 4-[(tert-butoxycarbonyl)amino]-5-{[tert-butyl(dimethyl)silyl]oxy}pentanoate

There total 8 articles about Methyl 4-[(tert-butoxycarbonyl)amino]-5-{[tert-butyl(dimethyl)silyl]oxy}pentanoate 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: 98.0%

tert-butyl (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidin-1-carboxylate (81658-26-6) → Methyl (4S)-4-(N-(tert-Butoxycarbonyl)amino)-5-((tert-butyldimethylsilyl)oxy)pentanoate (96014-55-0)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 0.166667h;

DOI:10.3762/bjoc.8.210

Reference yield: 92.0%

methyl (4S)-4-[(tert-butoxy)carbonylamino]-5-hydroxypentanoate (126587-35-7) + tert-butyldimethylsilyl chloride (18162-48-6) → Methyl (4S)-4-(N-(tert-Butoxycarbonyl)amino)-5-((tert-butyldimethylsilyl)oxy)pentanoate (96014-55-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

Reference yield:

L-glutamic acid 5-methyl ester (1499-55-4) → Methyl (4S)-4-(N-(tert-Butoxycarbonyl)amino)-5-((tert-butyldimethylsilyl)oxy)pentanoate (96014-55-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaHCO₃ / 1.) H₂O, 2.) 1,4-dioxane, 16 h, room temperature

2: DCC / ethyl acetate / 1.) 0 deg C, 2.) 3 h, room temperature

3: NaBH₄ / ethanol; tetrahydrofuran / 0.25 h / 0 °C

4: 92 percent / imidazole / dimethylformamide / 3 h / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00013a018

upstream raw materials:

(2S)-2-[(tert-butoxy)carbonylamino]-4-(methoxycarbonyl)butanoic acid

tert-butyldimethylsilyl chloride

methyl (4S)-4-[(tert-butoxy)carbonylamino]-5-hydroxypentanoate

L-glutamic acid 5-methyl ester

Downstream raw materials:

(S)-5-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-2-one

tert-butyl (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidin-1-carboxylate

(S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

(5S)-N-(tert-Butoxycarbonyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3-(phenylseleno)pyrrolidin-2-one