N-[(1,1-Dimethylethoxy)carbonyl]-O-[(4-nitrophenoxy)carbonyl]-L-serine 1,1-dimethylethyl ester

Base Information

• Chemical Name: N-[(1,1-Dimethylethoxy)carbonyl]-O-[(4-nitrophenoxy)carbonyl]-L-serine 1,1-dimethylethyl ester
• CAS No.: 186097-60-9
• Molecular Formula: C19H26N2O9
• Molecular Weight: 426.423
• DSSTox Substance ID: DTXSID901117881
• Mol file: 186097-60-9.mol

Synonyms:DTXSID901117881;186097-60-9;N-[(1,1-Dimethylethoxy)carbonyl]-O-[(4-nitrophenoxy)carbonyl]-L-serine 1,1-dimethylethyl ester

Chemical Property of N-[(1,1-Dimethylethoxy)carbonyl]-O-[(4-nitrophenoxy)carbonyl]-L-serine 1,1-dimethylethyl ester

Chemical Property:

• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 11
• Exact Mass: 426.16383041
• Heavy Atom Count: 30
• Complexity: 623

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C(COC(=O)OC1=CC=C(C=C1)[N+](=O)[O-])NC(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)(C)OC(=O)[C@H](COC(=O)OC1=CC=C(C=C1)[N+](=O)[O-])NC(=O)OC(C)(C)C

Technology Process of N-[(1,1-Dimethylethoxy)carbonyl]-O-[(4-nitrophenoxy)carbonyl]-L-serine 1,1-dimethylethyl ester

There total 2 articles about N-[(1,1-Dimethylethoxy)carbonyl]-O-[(4-nitrophenoxy)carbonyl]-L-serine 1,1-dimethylethyl 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: 79.0%

N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester (71630-31-4,7738-22-9) + 4-Nitrophenyl chloroformate (7693-46-1) → Boc-Glo(ONp)-(OtBu) (186097-60-9)

Guidance literature:

In pyridine; at 40 ℃; for 24h;

DOI:10.1002/ardp.19963291105

Reference yield: 9.0%

bis-(p-nitrophenyl) carbonate (5070-13-3) + N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester (71630-31-4,7738-22-9) → Boc-Glo(ONp)-(OtBu) (186097-60-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1016/S0968-0896(01)00269-3

Reference yield: 78.0%

Boc-Glo(ONp)-(OtBu) (186097-60-9) + H-Ser(Bzl)-Gly-O-t-Bu (3909-25-9) → Boc-Glo[-Ser(Bzl)-Gly-O-t-Bu]-O-t-Bu (675882-23-2)

Guidance literature:

In 1,4-dioxane; at 80 ℃; for 10h;

DOI:10.1016/S0014-827X(03)00135-6

upstream raw materials:

N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

4-Nitrophenyl chloroformate

bis-(p-nitrophenyl) carbonate

Downstream raw materials:

Boc-Glo[-Ser(Bzl)-Gly-O-t-Bu]-O-t-Bu

3-{2-(acetylamino-methylsulfanyl)-1-[(tert-butoxycarbonyl-phenyl-methyl)-carbamoyl]-ethylcarbamoyloxy}-2-tert-butoxycarbonylamino-propionic acid tert-butyl ester

C₅₆H₈₄N₆O₁₈S₂