(2S)-2-[3-[(2R)-2-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propanoylamino]propanoyloxy]-4-methylpentanoic acid

Base Information

• Chemical Name: (2S)-2-[3-[(2R)-2-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propanoylamino]propanoyloxy]-4-methylpentanoic acid
• CAS No.: 178977-41-8
• Molecular Formula: C₂₄H₃₆N₂O₈
• Molecular Weight: 480.558
• Mol file: 178977-41-8.mol

Synonyms:(2S)-2-[3-[(2R)-2-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propanoylamino]propanoyloxy]-4-methylpentanoic acid

Chemical Property of (2S)-2-[3-[(2R)-2-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propanoylamino]propanoyloxy]-4-methylpentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-2-[3-[(2R)-2-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propanoylamino]propanoyloxy]-4-methylpentanoic acid

There total 11 articles about (2S)-2-[3-[(2R)-2-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propanoylamino]propanoyloxy]-4-methylpentanoic acid 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: 89.0%

benzyl (2S)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionylamino]-propionyloxy]-4-methylpentanoate (219606-83-4) → (2S)-2-[3-[(2R)-2-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propanoylamino]propanoyloxy]-4-methylpentanoic acid (178977-41-8)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethyl acetate; at 20 ℃; for 2h;

DOI:10.1016/j.ejmech.2014.11.068

Reference yield:

(R)-2-hydroxy-4-methylpentanoic acid (20312-37-2,498-36-2) + 3-[2-tert-butoxycarbonylamino-3-(4-methoxy-phenyl)-propionylamino]-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester → (2S)-2-[3-[(2R)-2-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propanoylamino]propanoyloxy]-4-methylpentanoic acid (178977-41-8)

Guidance literature:

In acetonitrile; at 20 ℃; for 18h;

DOI:10.1021/jo000767+

Reference yield:

benzyl (2S)-2-hydroxy-4-methylpentanoate (37755-48-9,40298-04-2) → (2S)-2-[3-[(2R)-2-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propanoylamino]propanoyloxy]-4-methylpentanoic acid (178977-41-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / EDCI, DMAP

2: TFA / CH₂Cl₂ / 0 °C

3: 99 percent / EDCI, HOBT, Et₃N

4: H₂ / Pd(OH)2 / ethyl acetate

With dmap; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; palladium dihydroxide; In dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4039(98)02014-0

upstream raw materials:

(S)-2-hydroxyl-3,3-dimethylbutyric acid

3-[(2R)-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propanoylamino]propanoic acid

benzyl (2S)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionylamino]-propionyloxy]-4-methylpentanoate

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

Downstream raw materials:

desepoxyarenastatin A

tert-butyl (5S,6R)-5-[(2S)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-propionylamino]propionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate

dephenyldesepoxyarenastatin A

cryptophycin-24