(3R)-3-benzyloxycarbonylamino-2-[4-methoxybenzylsulfanyl]-5-[2,2-dimethylpropanoxy sulfonyl] pentanoic acid tert-butyl ester

Base Information

• Chemical Name: (3R)-3-benzyloxycarbonylamino-2-[4-methoxybenzylsulfanyl]-5-[2,2-dimethylpropanoxy sulfonyl] pentanoic acid tert-butyl ester
• CAS No.: 284486-62-0
• Molecular Formula: C₃₀H₄₃NO₈S₂
• Molecular Weight: 609.805
• Mol file: 284486-62-0.mol

Synonyms:(3R)-3-benzyloxycarbonylamino-2-[4-methoxybenzylsulfanyl]-5-[2,2-dimethylpropanoxy sulfonyl] pentanoic acid tert-butyl ester

Chemical Property of (3R)-3-benzyloxycarbonylamino-2-[4-methoxybenzylsulfanyl]-5-[2,2-dimethylpropanoxy sulfonyl] pentanoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R)-3-benzyloxycarbonylamino-2-[4-methoxybenzylsulfanyl]-5-[2,2-dimethylpropanoxy sulfonyl] pentanoic acid tert-butyl ester

There total 7 articles about (3R)-3-benzyloxycarbonylamino-2-[4-methoxybenzylsulfanyl]-5-[2,2-dimethylpropanoxy sulfonyl] pentanoic acid tert-butyl 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: 78.0%

(3R,4E)-3-benzyloxycarbonylamino-2-[4-methoxybenzylsulfanyl]-5-[2,2-dimethylpropanoxy sulfonyl]pent-4-enoic acid tert-butyl ester → (3R)-3-benzyloxycarbonylamino-2-[4-methoxybenzylsulfanyl]-5-[2,2-dimethylpropanoxy sulfonyl] pentanoic acid tert-butyl ester (284486-62-0)

Guidance literature:

With (triphenylphosphine)copper(I) hydride hexamer; water; In benzene; at 25 ℃; for 3h;

DOI:10.1016/S0040-4020(99)00922-9

Reference yield: 75.0%

(2R,3R), 3-benzyloxycarbonylamino-2-[4-methoxybenzylsulfanyl]-5-neopentyloxysulfonyl-pent-4-enoic acid tertiobutyl ester (263552-40-5) → (3R)-3-benzyloxycarbonylamino-2-[4-methoxybenzylsulfanyl]-5-[2,2-dimethylpropanoxy sulfonyl] pentanoic acid tert-butyl ester (284486-62-0)

Guidance literature:

With (triphenylphosphine)copper(I) hydride hexamer; water; at 25 ℃; for 3h;

DOI:10.1021/jm9903040

Reference yield:

(2S), 2-benzyloxycarbonylamino-succinic acid 1-methyl ester 4-tertiobutyl ester (63327-57-1) → (3R)-3-benzyloxycarbonylamino-2-[4-methoxybenzylsulfanyl]-5-[2,2-dimethylpropanoxy sulfonyl] pentanoic acid tert-butyl ester (284486-62-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 68 percent / n-BuLi

2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C

2.2: 68 percent / diisobutylaluminum hydride / hexane; tetrahydrofuran; toluene / 4 h / -78 - 20 °C

3.1: 75 percent / [(PPh₃)CuH]6; H₂O / 3 h / 25 °C

With n-butyllithium; (triphenylphosphine)copper(I) hydride hexamer; water; In tetrahydrofuran; hexane; 1.1: Metallation / 1.2: sulfenylation / 2.1: Metallation / 2.2: Dibal-H reduction-Wittig-Horner olefination / 3.1: Reduction;

DOI:10.1021/jm9903040

upstream raw materials:

(2R,3R), 3-benzyloxycarbonylamino-2-[4-methoxybenzylsulfanyl]-5-neopentyloxysulfonyl-pent-4-enoic acid tertiobutyl ester

Z-D(tBu)-OH

(2S), 2-benzyloxycarbonylamino-succinic acid 1-methyl ester 4-tertiobutyl ester

1-(4-methoxy-benzyldisulfanyl)-2,4-dinitrobenzene