N-[(1,1-Dimethylethoxy)carbonyl]-D-homoserine diphenylmethyl ester

Base Information

• Chemical Name: N-[(1,1-Dimethylethoxy)carbonyl]-D-homoserine diphenylmethyl ester
• CAS No.: 67198-88-3
• Molecular Formula: C₂₂H₂₇NO₅
• Molecular Weight: 385.46
• DSSTox Substance ID: DTXSID301165070
• Mol file: 67198-88-3.mol

Synonyms:SCHEMBL11272394;DTXSID301165070;N-[(1,1-Dimethylethoxy)carbonyl]-D-homoserine diphenylmethyl ester;67198-88-3

Chemical Property of N-[(1,1-Dimethylethoxy)carbonyl]-D-homoserine diphenylmethyl ester

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 385.18892296
• Heavy Atom Count: 28
• Complexity: 472

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CCO)C(=O)OC(C1=CC=CC=C1)C2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CCO)C(=O)OC(C1=CC=CC=C1)C2=CC=CC=C2

Technology Process of N-[(1,1-Dimethylethoxy)carbonyl]-D-homoserine diphenylmethyl ester

There total 6 articles about N-[(1,1-Dimethylethoxy)carbonyl]-D-homoserine diphenylmethyl 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: 64.0%

ethyl acetate benzene + N-t-butyloxycarbonyl D-homoserine sodium salt (67198-87-2) + Bromodiphenylmethane (776-74-9) → BOC-D-homoserine diphenylmethyl ester (67198-88-3)

Guidance literature:

In N,N,N,N,N,N-hexamethylphosphoric triamide; ethyl acetate;

Reference yield: 48.0%

BOC-D-aspartic acid 1-diphenylmethyl ester (88147-57-3) → BOC-D-homoserine diphenylmethyl ester (67198-88-3)

Guidance literature:

With borane; 1.) THF, 5 h, 0 degC, 2.) MeOH, R_.T_.;

DOI:10.1016/S0040-4020(01)92152-0

Reference yield:

N-t-butyloxycarbonyl-D-asparagine (7536-55-2,142847-17-4,75647-01-7) → BOC-D-homoserine diphenylmethyl ester (67198-88-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / dimethylformamide / 1.67 h / 40 - 50 °C

2: 50 percent / 1.) N₂O₄, NaOAc / 1.) AcOH, 5 h, R_.T_., 2.) benzene, 6 h, reflux

3: 48 percent / BH₃ / 1.) THF, 5 h, 0 degC, 2.) MeOH, R_.T_.

With borane; sodium acetate; dinitrogen tetraoxide; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)92152-0

upstream raw materials:

Bromodiphenylmethane

(R)-2-[(tert-butoxycarbonyl)amino]butano-4-lactone

BOC-D-aspartic acid 1-diphenylmethyl ester

N-t-butyloxycarbonyl-D-asparagine, benzhydrylester

Downstream raw materials:

(R)-2-tert-Butoxycarbonylamino-4-[4-(4-nitro-benzyloxyoxalyl)-phenoxy]-butyric acid benzhydryl ester

diphenylmethyl D-4-(p-acetylphenoxy)-2-(1-t-butoxyformamido)butyrate

-propoxy>phenyl>glyoxylic acid