dibenzyl 3(RS)-tert-butyloxycarbonyl-3-cinnamyl-2(R)-iso-butylsuccinate

Base Information

• Chemical Name: dibenzyl 3(RS)-tert-butyloxycarbonyl-3-cinnamyl-2(R)-iso-butylsuccinate
• CAS No.: 228261-86-7
• Molecular Formula: C₃₆H₄₂O₆
• Molecular Weight: 570.726
• Mol file: 228261-86-7.mol

Synonyms:dibenzyl 3(RS)-tert-butyloxycarbonyl-3-cinnamyl-2(R)-iso-butylsuccinate

Chemical Property of dibenzyl 3(RS)-tert-butyloxycarbonyl-3-cinnamyl-2(R)-iso-butylsuccinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dibenzyl 3(RS)-tert-butyloxycarbonyl-3-cinnamyl-2(R)-iso-butylsuccinate

There total 4 articles about dibenzyl 3(RS)-tert-butyloxycarbonyl-3-cinnamyl-2(R)-iso-butylsuccinate 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: 91.0%

Cinnamyl bromide (4392-24-9) + tert-butyl (2R)-1,2-dibenzyl 4-methylpentane-1,1,2-tricarboxylate (184948-24-1) → dibenzyl 3(RS)-tert-butyloxycarbonyl-3-cinnamyl-2(R)-iso-butylsuccinate (228261-86-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 5 ℃; for 15h;

DOI:10.1016/S0968-0896(02)00109-8

Reference yield:

(R)-leucine (328-38-1,21675-61-6,25248-98-0,70-45-1) → dibenzyl 3(RS)-tert-butyloxycarbonyl-3-cinnamyl-2(R)-iso-butylsuccinate (228261-86-7)

Guidance literature:

Multi-step reaction with 4 steps

1: HBr; sodium nitrite / H₂O / 3 h / 0 - 2 °C

2: 66 percent / p-toluenesulfonic acid monohydrate / toluene / 2 h / Heating

3: 89 percent / tert-butoxide / dimethylformamide / 15 h / 5 °C

4: 91 percent / sodium hydride / dimethylformamide / 15 h / 5 °C

With tert-butoxide; hydrogen bromide; sodium hydride; toluene-4-sulfonic acid; sodium nitrite; In water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0968-0896(02)00109-8

Reference yield:

(R)-2-bromo-4-methylpentanoic acid (42990-28-3) → dibenzyl 3(RS)-tert-butyloxycarbonyl-3-cinnamyl-2(R)-iso-butylsuccinate (228261-86-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / p-toluenesulfonic acid monohydrate / toluene / 2 h / Heating

2: 89 percent / tert-butoxide / dimethylformamide / 15 h / 5 °C

3: 91 percent / sodium hydride / dimethylformamide / 15 h / 5 °C

With tert-butoxide; sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0968-0896(02)00109-8

upstream raw materials:

Cinnamyl bromide

tert-butyl (2R)-1,2-dibenzyl 4-methylpentane-1,1,2-tricarboxylate

(R)-leucine

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

Downstream raw materials:

3(S)-tert-butyloxycarbonyl-6-phenyl-2(R)-isobutylhexanoic acid

tert-butyl 3(R)-hydroxymethyl-5-methyl-2(S)-phenylpropylhexanoate