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

Base Information

• Chemical Name: (2R,3R), 3-benzyloxycarbonylamino-2-[4-methoxybenzylsulfanyl]-5-neopentyloxysulfonyl-pent-4-enoic acid tertiobutyl ester
• CAS No.: 263552-40-5
• Molecular Formula: C₃₀H₄₁NO₈S₂
• Molecular Weight: 607.789
• Mol file: 263552-40-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (2R,3R), 3-benzyloxycarbonylamino-2-[4-methoxybenzylsulfanyl]-5-neopentyloxysulfonyl-pent-4-enoic acid tertiobutyl 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: 68.0%

neopentyl diethoxyphosphorylmethanesulfonate + (2R,3R), 2-benzyloxycarbonylamino, 3-(4-methoxybenzylsulfanyl)-succinic acid 1-methyl ester 4-tertiobutyl ester (263552-35-8) → (2R,3R), 3-benzyloxycarbonylamino-2-[4-methoxybenzylsulfanyl]-5-neopentyloxysulfonyl-pent-4-enoic acid tertiobutyl ester (263552-40-5)

Guidance literature:

neopentyl diethoxyphosphorylmethanesulfonate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

(2R,3R), 2-benzyloxycarbonylamino, 3-(4-methoxybenzylsulfanyl)-succinic acid 1-methyl ester 4-tertiobutyl ester; With diisobutylaluminium hydride; In tetrahydrofuran; hexane; toluene; at -78 - 20 ℃; for 4h;

DOI:10.1021/jm9903040

Reference yield:

Z-D(tBu)-OH (5545-52-8) → (2R,3R), 3-benzyloxycarbonylamino-2-[4-methoxybenzylsulfanyl]-5-neopentyloxysulfonyl-pent-4-enoic acid tertiobutyl ester (263552-40-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 99 percent

2.1: 68 percent / n-BuLi

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

3.2: 68 percent / diisobutylaluminum hydride / hexane; tetrahydrofuran; toluene / 4 h / -78 - 20 °C

With n-butyllithium; In tetrahydrofuran; hexane; 1.1: Methylation / 2.1: Metallation / 2.2: sulfenylation / 3.1: Metallation / 3.2: Dibal-H reduction-Wittig-Horner olefination;

DOI:10.1021/jm9903040

Reference yield:

(2S), 2-benzyloxycarbonylamino-succinic acid 1-methyl ester 4-tertiobutyl ester (63327-57-1) → (2R,3R), 3-benzyloxycarbonylamino-2-[4-methoxybenzylsulfanyl]-5-neopentyloxysulfonyl-pent-4-enoic acid tertiobutyl ester (263552-40-5)

Guidance literature:

Multi-step reaction with 2 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

With n-butyllithium; In tetrahydrofuran; hexane; 1.1: Metallation / 1.2: sulfenylation / 2.1: Metallation / 2.2: Dibal-H reduction-Wittig-Horner olefination;

DOI:10.1021/jm9903040

upstream raw materials:

(2R,3R), 2-benzyloxycarbonylamino, 3-(4-methoxybenzylsulfanyl)-succinic acid 1-methyl ester 4-tertiobutyl ester

Z-D(tBu)-OH

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

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

Downstream raw materials:

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