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

Base Information

• Chemical Name: Methyl 4-{[(benzyloxy)carbonyl]amino}-5-{[tert-butyl(dimethyl)silyl]oxy}pentanoate
• CAS No.: 911050-87-8
• Molecular Formula: C20H33NO5Si
• Molecular Weight: 395.57
• DSSTox Substance ID: DTXSID80694709
• Mol file: 911050-87-8.mol

Synonyms:DTXSID80694709;Methyl 4-{[(benzyloxy)carbonyl]amino}-5-{[tert-butyl(dimethyl)silyl]oxy}pentanoate

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

Chemical Property:

• Refractive Index: 1.487
• Boiling Point: 468 °C at 760 mmHg
• Flash Point: 236.8 °C
• PSA: 73.86000
• Density: 1.044 g/cm³
• LogP: 4.64730
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 395.21279969
• Heavy Atom Count: 27
• Complexity: 470

Purity/Quality:

99% ^*data from raw suppliers

(S)-METHYL 4-(BENZYLOXYCARBONYLAMINO)-5-(TERT-BUTYLDIMETHYLSILYLOXY)PENTANOATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OCC(CCC(=O)OC)NC(=O)OCC1=CC=CC=C1

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

There total 1 articles about Methyl 4-{[(benzyloxy)carbonyl]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: 74.0%

4-(S)-[4-(N-benzyloxycarbonylamino)-5-hydroxy]pentanoic acid methyl ester (119109-58-9) + tert-butyldimethylsilyl chloride (18162-48-6) → methyl (4S)-4-[(benzyloxy)carbonyl]amino-5-{[tert-butyldimethylsilyl]oxy}pentanoate (911050-87-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1016/j.bmc.2006.05.040

Reference yield: 52.0%

methyl (4S)-4-[(benzyloxy)carbonyl]amino-5-{[tert-butyldimethylsilyl]oxy}pentanoate (911050-87-8) + methyl iodide (74-88-4) → methyl (2S,4S)-4-[(benzyloxy)carbonyl]amino-5-[tert-butyldimethylsilyl]oxy-2-methylpentanoate (911050-89-0)

Guidance literature:

methyl (4S)-4-[(benzyloxy)carbonyl]amino-5-{[tert-butyldimethylsilyl]oxy}pentanoate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

methyl iodide; In tetrahydrofuran; at -78 ℃; for 3h;

DOI:10.1016/j.bmc.2006.05.040

Reference yield:

methyl (4S)-4-[(benzyloxy)carbonyl]amino-5-{[tert-butyldimethylsilyl]oxy}pentanoate (911050-87-8) → methyl (2S,4S)-5-[tert-butyldimethylsilyl]oxy-2-methyl-4-[(4-phenoxybenzoyl)amino]pentanoate (911050-91-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hexamethyldisilazide / tetrahydrofuran / 1 h / -78 °C

1.2: 52 percent / tetrahydrofuran / 3 h / -78 °C

2.1: hydrogen / Pd/C / methanol / 1 h

3.1: 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl; 1-hydroxybenzotriazole monohydrate; triethylamine / dimethylformamide / 3 h / 20 °C

With hydrogen; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2006.05.040

upstream raw materials:

4-(S)-[4-(N-benzyloxycarbonylamino)-5-hydroxy]pentanoic acid methyl ester

tert-butyldimethylsilyl chloride

Downstream raw materials:

methyl (2S,4S)-4-[(benzyloxy)carbonyl]amino-5-[tert-butyldimethylsilyl]oxy-2-methylpentanoate

methyl (2S,4S)-5-[tert-butyldimethylsilyl]oxy-2-methyl-4-[(4-phenoxybenzoyl)amino]pentanoate

(2S,4S)-5-[tert-butyldimethylsilyl]oxy-2-methyl-4-[(4-phenoxybenzoyl)amino]pentanoic acid

ONO-M₁₁-335

Refernces