(S)-3-tert-Butoxycarbonylamino-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Base Information

• Chemical Name: (S)-3-tert-Butoxycarbonylamino-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester
• CAS No.: 110575-50-3
• Molecular Formula: C₂₈H₄₃N₃O₆
• Molecular Weight: 517.666
• Mol file: 110575-50-3.mol

Synonyms:(S)-3-tert-Butoxycarbonylamino-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Chemical Property of (S)-3-tert-Butoxycarbonylamino-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-3-tert-Butoxycarbonylamino-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

There total 1 articles about (S)-3-tert-Butoxycarbonylamino-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl 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: 76.0%

L-Phenylalanine amide (5241-58-7) + Boc-Asp(OMen)-OSu (110575-49-0) → (S)-3-tert-Butoxycarbonylamino-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (110575-50-3)

Guidance literature:

With 4-methyl-morpholine; In N,N-dimethyl-formamide;

Reference yield: 100.0%

(S)-3-tert-Butoxycarbonylamino-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (110575-50-3) → Asp-Phe-NH2 (5241-71-4)

Guidance literature:

With trifluorormethanesulfonic acid; methyl-phenyl-thioether; diphenyl sulfide; In trifluoroacetic acid; at 0 ℃; for 2h;

Reference yield:

(S)-3-tert-Butoxycarbonylamino-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (110575-50-3) → H-Trp-Met-Asc-Phe-NH2 (110575-53-6,111004-09-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) DCC, HONB; 2.) NMM, Et₃N, TFA / 1.) THF-DMF, 4 h; 2.) DMF, overnight

2: 1.) DCC, HOSu; 2.) NMM, Et₃N, TFA / 1.) THF, 5 h; 2.) DMF, overnight

3: 95 percent / trimethylphenylthiosilane / dimethylformamide / 0.25 h / 40 °C

4: 6 percent / 1 M TFMSA-thioanisole, EDT / trifluoroacetic acid / 2 h

With 4-methyl-morpholine; 1-hydroxy-pyrrolidine-2,5-dione; ethylenediaminetetraacetic acid; trifluorormethanesulfonic acid; methyl-phenyl-thioether; phenylthiotrimethylsilane; triethylamine; dicyclohexyl-carbodiimide; (3aR,4R,7S,7aS)-2-hydroxy-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione (N-hydroxy-5-exo-norbornene-2,3-dicarboximide); trifluoroacetic acid; In N,N-dimethyl-formamide; trifluoroacetic acid;

upstream raw materials:

L-Phenylalanine amide

Boc-Asp(OMen)-OSu

Downstream raw materials:

Z(OMe)-Met(O)-Asp(OMen)-Phe-NH₂

Asp-Phe-NH₂

cholecystokinin-4

H-Trp-Met-Asc-Phe-NH₂

Refernces