N-((1,1-Dimethylethoxy)carbonyl)-β-Ala-O-D-Leu diphenylmethyl ester

Base Information

• Chemical Name: N-((1,1-Dimethylethoxy)carbonyl)-β-Ala-O-D-Leu diphenylmethyl ester
• CAS No.: 168070-00-6
• Molecular Formula: C₂₇H₃₅NO₆
• Molecular Weight: 469.578
• Mol file: 168070-00-6.mol

Synonyms:N-((1,1-Dimethylethoxy)carbonyl)-β-Ala-O-D-Leu diphenylmethyl ester

Chemical Property of N-((1,1-Dimethylethoxy)carbonyl)-β-Ala-O-D-Leu diphenylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-((1,1-Dimethylethoxy)carbonyl)-β-Ala-O-D-Leu diphenylmethyl ester

There total 3 articles about N-((1,1-Dimethylethoxy)carbonyl)-β-Ala-O-D-Leu 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: 96.0%

3-(tert-butyloxycarbonylamino)propionic acid (3303-84-2) + Diphenylmethyl (2R)-2-hydroxy-4-methylpentanoate (168069-99-6) → N-((1,1-Dimethylethoxy)carbonyl)-β-Ala-O-D-Leu diphenylmethyl ester (168070-00-6)

Guidance literature:

With dmap; Isopropenyl chloroformate; triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/jo00124a019

Reference yield:

(R)-2-hydroxy-4-methylpentanoic acid (20312-37-2,498-36-2) → N-((1,1-Dimethylethoxy)carbonyl)-β-Ala-O-D-Leu diphenylmethyl ester (168070-00-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / PhI(OAc)2, I₂ / -10 °C

2: EDCI, DMAP, TEA

With dmap; [bis(acetoxy)iodo]benzene; TEA; iodine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;

DOI:10.1016/S0960-894X(99)00038-4

Reference yield:

(R)-leucine (328-38-1,21675-61-6,25248-98-0,70-45-1) → N-((1,1-Dimethylethoxy)carbonyl)-β-Ala-O-D-Leu diphenylmethyl ester (168070-00-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 51 percent / NaNO₂, H₂SO₄ / H₂O

2: 70 percent / PhI(OAc)2, I₂ / -10 °C

3: EDCI, DMAP, TEA

With dmap; [bis(acetoxy)iodo]benzene; TEA; sulfuric acid; iodine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium nitrite; In water;

DOI:10.1016/S0960-894X(99)00038-4

upstream raw materials:

3-(tert-butyloxycarbonylamino)propionic acid

Diphenylmethyl (2R)-2-hydroxy-4-methylpentanoate

(R)-leucine

(R)-2-hydroxy-4-methylpentanoic acid

Downstream raw materials:

N-((1,1-Dimethylethoxy)carbonyl)-β-Ala-O-D-Leu-L-Leu-O-L-Leu-N(Me)-L-Phe phenylmethyl ester

H-β-Ala-O-D-Leu-L-Leu-O-L-Leu-N(Me)-L-Phe phenylmethyl ester

H-β-Ala-O-D-Leu-L-Leu-O-L-Leu-N(Me)-L-Phe-OH

leualacin

Refernces

• 1、 McLaren. "Total synthesis of the cyclic depsipeptide leualacin". . p. 6082 - 6084. Retrieved 2007/10/03.