(2S,2'R)-benzyl 2-[(3'-{[(tert-butoxy)carbonyl]amino}propionyl)oxy]-4-methylpentanoate

Base Information

• Chemical Name: (2S,2'R)-benzyl 2-[(3'-{[(tert-butoxy)carbonyl]amino}propionyl)oxy]-4-methylpentanoate
• CAS No.: 219606-82-3
• Molecular Formula: C₂₁H₃₁NO₆
• Molecular Weight: 393.48
• Mol file: 219606-82-3.mol

Synonyms:(2S,2'R)-benzyl 2-[(3'-{[(tert-butoxy)carbonyl]amino}propionyl)oxy]-4-methylpentanoate

Chemical Property of (2S,2'R)-benzyl 2-[(3'-{[(tert-butoxy)carbonyl]amino}propionyl)oxy]-4-methylpentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,2'R)-benzyl 2-[(3'-{[(tert-butoxy)carbonyl]amino}propionyl)oxy]-4-methylpentanoate

There total 3 articles about (2S,2'R)-benzyl 2-[(3'-{[(tert-butoxy)carbonyl]amino}propionyl)oxy]-4-methylpentanoate 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: 99.0%

3-(tert-butyloxycarbonylamino)propionic acid (3303-84-2) + benzyl (2S)-2-hydroxy-4-methylpentanoate (37755-48-9,40298-04-2) → (2S,2'R)-benzyl 2-[(3'-{[(tert-butoxy)carbonyl]amino}propionyl)oxy]-4-methylpentanoate (219606-82-3)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;

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

Reference yield:

(S)-2-hydroxyl-3,3-dimethylbutyric acid (13748-90-8,498-36-2) → (2S,2'R)-benzyl 2-[(3'-{[(tert-butoxy)carbonyl]amino}propionyl)oxy]-4-methylpentanoate (219606-82-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Cs₂CO₃ / methanol; H₂O / 30 h / 23 °C

1.2: 100 percent / dimethylformamide / 12 h / 20 °C

2.1: 91 percent / DCC; DMAP / CH₂Cl₂ / 12 h / 23 °C

With dmap; caesium carbonate; dicyclohexyl-carbodiimide; In methanol; dichloromethane; water;

DOI:10.1002/ejoc.200300814

Reference yield:

L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) → (2S,2'R)-benzyl 2-[(3'-{[(tert-butoxy)carbonyl]amino}propionyl)oxy]-4-methylpentanoate (219606-82-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium nitrite; sulfuric acid / water / 0 - 20 °C

2.1: caesium carbonate / methanol; water / 0.5 h / 20 °C

2.2: 12 h / 20 °C

3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 18 h / 0 - 20 °C

With dmap; sulfuric acid; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium nitrite; In methanol; dichloromethane; water;

DOI:10.1016/j.ejmech.2014.11.068

upstream raw materials:

3-(tert-butyloxycarbonylamino)propionic acid

benzyl (2S)-2-hydroxy-4-methylpentanoate

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

L-leucine

Downstream raw materials:

desepoxyarenastatin A

cryptophycin-24

(2S,1''S,2''R,1''''R)-1''-[3'''-({1''''-[(tert-butoxy)carbonyl]-2''''-(p-methoxyphenyl)ethyl}carbamoyl)allyl]-2''-methyl-4''-phenylbut-3''-enyl 2-[(3'-{[(tert-butoxy)carbonyl]amino}propionyl)oxy]-4-methylpentanoate

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