(2R)-3-benzyloxy-2-((2S)-3-benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)propionic acid methyl ester

Base Information

• Chemical Name: (2R)-3-benzyloxy-2-((2S)-3-benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)propionic acid methyl ester
• CAS No.: 752251-21-1
• Molecular Formula: C₂₇H₃₆N₂O₇
• Molecular Weight: 500.592
• Mol file: 752251-21-1.mol

Synonyms:(2R)-3-benzyloxy-2-((2S)-3-benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)propionic acid methyl ester

Chemical Property of (2R)-3-benzyloxy-2-((2S)-3-benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-3-benzyloxy-2-((2S)-3-benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)propionic acid methyl ester

There total 2 articles about (2R)-3-benzyloxy-2-((2S)-3-benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)propionic acid methyl 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:

N-Boc-O-benzyl-L-threonine (15260-10-3) + (2R)-3-benzyloxy-2-aminopropanoic acid methyl ester (84907-81-3) → (2R)-3-benzyloxy-2-((2S)-3-benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)propionic acid methyl ester (752251-21-1)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃;

DOI:10.1002/anie.200453909

Reference yield:

(R)-3-benzyloxy-2-tert-butoxycarbonyl-amino-propionic acid methyl ester (67389-47-3) → (2R)-3-benzyloxy-2-((2S)-3-benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)propionic acid methyl ester (752251-21-1)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / CH₂Cl₂ / 2.5 h / 0 - 20 °C

2: 663 mg / EDC*HCl; HOBt; N-methylmorpholine / CH₂Cl₂ / 20 °C

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane;

DOI:10.1002/anie.200453909

Reference yield: 70.0%

(2R)-3-benzyloxy-2-((2S)-3-benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)propionic acid methyl ester (752251-21-1) → (2R)-3-benzyloxy-2-((2S)-3-benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)propionic acid (752251-20-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 1.5h;

DOI:10.1002/anie.200453909

upstream raw materials:

N-Boc-O-benzyl-L-threonine

(2R)-3-benzyloxy-2-aminopropanoic acid methyl ester

(R)-3-benzyloxy-2-tert-butoxycarbonyl-amino-propionic acid methyl ester

Downstream raw materials:

(2R)-3-benzyloxy-2-((2S)-3-benzyloxy-2-tert-butoxycarbonylamino-butyrylamino)propionic acid

H-L-Thr(OBn)-D-Ser(OBn)-LSer(OBn)-(3S)-THQ(OBn)

(S)-3-amino-6,7-bis(OBn)-1,1-dimethyl-1,2,3,4-tetrahydroquinolin-1-ium L-ser(OBn)-D-ser (OBn)-BocL-thr(OBn)