tert-butyl (2R,5S,3E)-2-[4-(tert-butyldimethylsiloxy)butyl]-9-[N-(2-chlorobenzyloxycarbonyl)amino]-5-[N-(2-nitrophenylsulfonyl)amino]non-3-enoate

Base Information

• Chemical Name: tert-butyl (2R,5S,3E)-2-[4-(tert-butyldimethylsiloxy)butyl]-9-[N-(2-chlorobenzyloxycarbonyl)amino]-5-[N-(2-nitrophenylsulfonyl)amino]non-3-enoate
• CAS No.: 1186125-44-9
• Molecular Formula: C₃₇H₅₆ClN₃O₉SSi
• Molecular Weight: 782.471

Synonyms:tert-butyl (2R,5S,3E)-2-[4-(tert-butyldimethylsiloxy)butyl]-9-[N-(2-chlorobenzyloxycarbonyl)amino]-5-[N-(2-nitrophenylsulfonyl)amino]non-3-enoate

Chemical Property of tert-butyl (2R,5S,3E)-2-[4-(tert-butyldimethylsiloxy)butyl]-9-[N-(2-chlorobenzyloxycarbonyl)amino]-5-[N-(2-nitrophenylsulfonyl)amino]non-3-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of tert-butyl (2R,5S,3E)-2-[4-(tert-butyldimethylsiloxy)butyl]-9-[N-(2-chlorobenzyloxycarbonyl)amino]-5-[N-(2-nitrophenylsulfonyl)amino]non-3-enoate

There total 7 articles about tert-butyl (2R,5S,3E)-2-[4-(tert-butyldimethylsiloxy)butyl]-9-[N-(2-chlorobenzyloxycarbonyl)amino]-5-[N-(2-nitrophenylsulfonyl)amino]non-3-enoate 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: 60.0%

tert-butyl (4R,5S,2E)-9-[N-(2-chlorobenzyloxycarbonyl)amino]-4,5-[N-(2-nitrophenylsulfonyl)epimino]non-2-enoate (1186125-43-8) + 1-{[dimethyl(1,1-dimethylethyl)silyl]oxy}-4-iodobutane (92511-12-1) → tert-butyl (2R,5S,3E)-2-[4-(tert-butyldimethylsiloxy)butyl]-9-[N-(2-chlorobenzyloxycarbonyl)amino]-5-[N-(2-nitrophenylsulfonyl)amino]non-3-enoate (1186125-44-9)

Guidance literature:

1-{[dimethyl(1,1-dimethylethyl)silyl]oxy}-4-iodobutane; With tert.-butyl lithium; In diethyl ether; at -78 ℃; for 0.5h; Inert atmosphere;

With copper(l) cyanide; lithium chloride; In tetrahydrofuran; diethyl ether; at -78 - 0 ℃; Inert atmosphere;

tert-butyl (4R,5S,2E)-9-[N-(2-chlorobenzyloxycarbonyl)amino]-4,5-[N-(2-nitrophenylsulfonyl)epimino]non-2-enoate; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1.5h; stereoselective reaction;

DOI:10.1039/b907983a

Reference yield:

C16H23ClN2O3 → tert-butyl (2R,5S,3E)-2-[4-(tert-butyldimethylsiloxy)butyl]-9-[N-(2-chlorobenzyloxycarbonyl)amino]-5-[N-(2-nitrophenylsulfonyl)amino]non-3-enoate (1186125-44-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 2,4,6-trimethyl-pyridine / chloroform / 1.5 h / 0 - 20 °C

2.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 4 h / 0 - 20 °C / Inert atmosphere

3.1: ozone / ethyl acetate / -78 °C

3.2: 0.08 h / -78 °C

4.1: N-ethyl-N,N-diisopropylamine; lithium chloride / acetonitrile / 1 h / 0 °C / Inert atmosphere

4.2: 3 h / 0 - 20 °C / Inert atmosphere

5.1: tert.-butyl lithium / diethyl ether / 0.5 h / -78 °C / Inert atmosphere

5.2: -78 - 0 °C / Inert atmosphere

5.3: 1.5 h / -78 °C

With 2,4,6-trimethyl-pyridine; di-isopropyl azodicarboxylate; tert.-butyl lithium; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; diethyl ether; chloroform; ethyl acetate; toluene; acetonitrile; 2.1: Mitsunobu reaction;

DOI:10.1039/b907983a

Reference yield:

(3R,4S)-8-[N-(2-chlorobenzyloxycarbonyl)amino]-3,4-[N-(2-nitrophenylsulfonyl)epimino]oct-1-ene (1186125-42-7) → tert-butyl (2R,5S,3E)-2-[4-(tert-butyldimethylsiloxy)butyl]-9-[N-(2-chlorobenzyloxycarbonyl)amino]-5-[N-(2-nitrophenylsulfonyl)amino]non-3-enoate (1186125-44-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: ozone / ethyl acetate / -78 °C

1.2: 0.08 h / -78 °C

2.1: N-ethyl-N,N-diisopropylamine; lithium chloride / acetonitrile / 1 h / 0 °C / Inert atmosphere

2.2: 3 h / 0 - 20 °C / Inert atmosphere

3.1: tert.-butyl lithium / diethyl ether / 0.5 h / -78 °C / Inert atmosphere

3.2: -78 - 0 °C / Inert atmosphere

3.3: 1.5 h / -78 °C

With tert.-butyl lithium; ozone; N-ethyl-N,N-diisopropylamine; lithium chloride; In diethyl ether; ethyl acetate; acetonitrile;

DOI:10.1039/b907983a

upstream raw materials:

(3S,4S)-8-[N-(2-chlorobenzyloxycarbonyl)amino]-4-[N-(2-nitrophenylsulfonyl)amino]oct-1-ene-3-ol

C₂₁H₃₁ClN₂O₅

(3R,4S)-8-[N-(2-chlorobenzyloxycarbonyl)amino]-3,4-[N-(2-nitrophenylsulfonyl)epimino]oct-1-ene

tert-butyl (4R,5S,2E)-9-[N-(2-chlorobenzyloxycarbonyl)amino]-4,5-[N-(2-nitrophenylsulfonyl)epimino]non-2-enoate

Downstream raw materials:

(2R,5S,3E)-5-[N-(9-fluorenylmethoxycarbonyl)amino]-2-{4-[N-(benzyloxycarbonyl)amino]butyl}-9-[N-(2-chlorobenzyloxycarbonyl)amino]non-3-enoic acid

tert-butyl (2R,5S,3E)-2-{4-[N-(benzyloxycarbonyl)-N-(2-nitrophenylsulfonyl)amino]butyl}-9-[N-(2-chlorobenzyloxycarbonyl)amino]-5-[N-(2-nitrophenylsulfonyl)amino]non-3-enoate

tert-butyl (2R,5S,3E)-5-[N-(9-fluorenylmethoxycarbonyl)amino]-2-{4-[N-(benzyloxycarbonyl)amino]butyl}-9-[N-(2-chlorobenzyloxycarbonyl)amino]non-3-enoate

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