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

Base Information

Chemical Name:(2R,5S,3E)-5-[N-(9-fluorenylmethoxycarbonyl)amino]-2-{4-[N-(benzyloxycarbonyl)amino]butyl}-9-[N-(2-chlorobenzyloxycarbonyl)amino]non-3-enoic acid
CAS No.:1186125-47-2
Molecular Formula:C₄₄H₄₈ClN₃O₈
Molecular Weight:782.333
Hs Code.:

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

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

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

There total 11 articles about (2R,5S,3E)-5-[N-(9-fluorenylmethoxycarbonyl)amino]-2-{4-[N-(benzyloxycarbonyl)amino]butyl}-9-[N-(2-chlorobenzyloxycarbonyl)amino]non-3-enoic acid 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: 96.0%

: 1186125-46-1
tert-butyl (2R,5S,3E)-5-[N-(9-fluorenylmethoxycarbonyl)amino]-2-{4-[N-(benzyloxycarbonyl)amino]butyl}-9-[N-(2-chlorobenzyloxycarbonyl)amino]non-3-enoate

: 1186125-47-2
(2R,5S,3E)-5-[N-(9-fluorenylmethoxycarbonyl)amino]-2-{4-[N-(benzyloxycarbonyl)amino]butyl}-9-[N-(2-chlorobenzyloxycarbonyl)amino]non-3-enoic acid

Guidance literature:: With hydrogenchloride; water; In 1,4-dioxane; at 0 - 20 ℃; for 20h;
DOI:10.1039/b907983a

Reference yield:

: C₁₆H₂₃ClN₂O₃

: 1186125-47-2
(2R,5S,3E)-5-[N-(9-fluorenylmethoxycarbonyl)amino]-2-{4-[N-(benzyloxycarbonyl)amino]butyl}-9-[N-(2-chlorobenzyloxycarbonyl)amino]non-3-enoic acid

Guidance literature:: Multi-step reaction with 10 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

6.1: fluorosilicic acid / methanol; acetonitrile / 0.5 h / 0 °C

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

8.1: potassium carbonate; thiophenol / N,N-dimethyl-formamide / 3 h / 0 - 20 °C

9.1: triethylamine / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C

10.1: hydrogenchloride; water / 1,4-dioxane / 20 h / 0 - 20 °C

With 2,4,6-trimethyl-pyridine; hydrogenchloride; fluorosilicic acid; di-isopropyl azodicarboxylate; water; tert.-butyl lithium; potassium carbonate; ozone; thiophenol; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; chloroform; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 2.1: Mitsunobu reaction;
DOI:10.1039/b907983a

Reference yield:

: 1186125-41-6
(3S,4S)-8-[N-(2-chlorobenzyloxycarbonyl)amino]-4-[N-(2-nitrophenylsulfonyl)amino]oct-1-ene-3-ol

: 1186125-47-2
(2R,5S,3E)-5-[N-(9-fluorenylmethoxycarbonyl)amino]-2-{4-[N-(benzyloxycarbonyl)amino]butyl}-9-[N-(2-chlorobenzyloxycarbonyl)amino]non-3-enoic acid

Guidance literature:: Multi-step reaction with 9 steps

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

2.1: ozone / ethyl acetate / -78 °C

2.2: 0.08 h / -78 °C

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

3.2: 3 h / 0 - 20 °C / Inert atmosphere

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

4.2: -78 - 0 °C / Inert atmosphere

4.3: 1.5 h / -78 °C

5.1: fluorosilicic acid / methanol; acetonitrile / 0.5 h / 0 °C

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

7.1: potassium carbonate; thiophenol / N,N-dimethyl-formamide / 3 h / 0 - 20 °C

8.1: triethylamine / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C

9.1: hydrogenchloride; water / 1,4-dioxane / 20 h / 0 - 20 °C

With hydrogenchloride; fluorosilicic acid; di-isopropyl azodicarboxylate; water; tert.-butyl lithium; potassium carbonate; ozone; thiophenol; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Mitsunobu reaction;
DOI:10.1039/b907983a