L-Leucine, N-[N-[1,4-dioxo-6-[2-[2-[4-(phenylmethoxy)phenyl]-1-[[(2,2,2-trichloroeth oxy)carbonyl]amino]ethyl]-1,3-dioxolan-2-yl]hexyl]-L-phenylalanyl]-, (S)-

Base Information

• Chemical Name: L-Leucine, N-[N-[1,4-dioxo-6-[2-[2-[4-(phenylmethoxy)phenyl]-1-[[(2,2,2-trichloroeth oxy)carbonyl]amino]ethyl]-1,3-dioxolan-2-yl]hexyl]-L-phenylalanyl]-, (S)-
• CAS No.: 88036-22-0
• Molecular Formula: C42H50Cl3N3O10
• Molecular Weight: 863.232

Synonyms:

Chemical Property of L-Leucine, N-[N-[1,4-dioxo-6-[2-[2-[4-(phenylmethoxy)phenyl]-1-[[(2,2,2-trichloroeth oxy)carbonyl]amino]ethyl]-1,3-dioxolan-2-yl]hexyl]-L-phenylalanyl]-, (S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Leucine, N-[N-[1,4-dioxo-6-[2-[2-[4-(phenylmethoxy)phenyl]-1-[[(2,2,2-trichloroeth oxy)carbonyl]amino]ethyl]-1,3-dioxolan-2-yl]hexyl]-L-phenylalanyl]-, (S)-

There total 10 articles about L-Leucine, N-[N-[1,4-dioxo-6-[2-[2-[4-(phenylmethoxy)phenyl]-1-[[(2,2,2-trichloroeth oxy)carbonyl]amino]ethyl]-1,3-dioxolan-2-yl]hexyl]-L-phenylalanyl]-, (S)- 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: 62.6%

5-<2-<2-<4-(benzyloxy)phenyl>-1(S)-<<(2,2,2-trichloroethyloxy)carbonyl>amino>ethyl>-1,3-dioxolan-2-yl>-3-oxopentanoyl-L-phenylalanyl-L-leucine methyl ester (88036-21-9) → 5-<2-<2-<4-(benzyloxy)phenyl>-1(S)-<<(2,2,2-trichloroethoxy)carbonyl>amino>ethyl>-1,3-dioxolan-2-yl>-3-oxopentanoyl-L-phenylalanyl-L-leucine (88036-22-0)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; for 1.5h;

DOI:10.1021/jm00368a003

Reference yield:

(S)-Nα-phthaloyl-O-benzyltyrosine (2130-97-4) → 5-<2-<2-<4-(benzyloxy)phenyl>-1(S)-<<(2,2,2-trichloroethoxy)carbonyl>amino>ethyl>-1,3-dioxolan-2-yl>-3-oxopentanoyl-L-phenylalanyl-L-leucine (88036-22-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 93 percent / PCl₅ / benzene / 1 h / 55 °C

2: 1.) Mg / 1.) THF, 40 deg C, 45 min, 2.) THF, RT, 1 h

3: 64.5 percent / p-toluenesulfonic acid / toluene / 6 h

4: 76.9 percent / p-toluenesulfonic acid / acetone / 32 h / Ambient temperature

5: 1.) Mg / 1.) THF, 40 deg C, 45 min, 2.) THF, RT, 15 min

6: 99.3 percent / hydrazine / ethanol / 15 h / Heating

7: N,N-diisopropylethylamine / CH₂Cl₂ / 0.25 h / 0 °C

8: CrO₃, 35percent H₂SO₄ / acetone / 0.5 h / 0 °C

9: 55.9 percent / 1-hydroxybenzotriazole, Et₃N, dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 64 h / Ambient temperature

10: 62.6 percent / 1 N aq. NaOH / tetrahydrofuran / 1.5 h

With chromium(VI) oxide; sodium hydroxide; phosphorus pentachloride; sulfuric acid; benzotriazol-1-ol; toluene-4-sulfonic acid; magnesium; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; hydrazine; In tetrahydrofuran; ethanol; dichloromethane; acetone; toluene; benzene;

DOI:10.1021/jm00368a003

Reference yield:

(S)-Nα-phthaloyl-O-benzyltyrosine chloride (88036-14-0) → 5-<2-<2-<4-(benzyloxy)phenyl>-1(S)-<<(2,2,2-trichloroethoxy)carbonyl>amino>ethyl>-1,3-dioxolan-2-yl>-3-oxopentanoyl-L-phenylalanyl-L-leucine (88036-22-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) Mg / 1.) THF, 40 deg C, 45 min, 2.) THF, RT, 1 h

2: 64.5 percent / p-toluenesulfonic acid / toluene / 6 h

3: 76.9 percent / p-toluenesulfonic acid / acetone / 32 h / Ambient temperature

4: 1.) Mg / 1.) THF, 40 deg C, 45 min, 2.) THF, RT, 15 min

5: 99.3 percent / hydrazine / ethanol / 15 h / Heating

6: N,N-diisopropylethylamine / CH₂Cl₂ / 0.25 h / 0 °C

7: CrO₃, 35percent H₂SO₄ / acetone / 0.5 h / 0 °C

8: 55.9 percent / 1-hydroxybenzotriazole, Et₃N, dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 64 h / Ambient temperature

9: 62.6 percent / 1 N aq. NaOH / tetrahydrofuran / 1.5 h

With chromium(VI) oxide; sodium hydroxide; sulfuric acid; benzotriazol-1-ol; toluene-4-sulfonic acid; magnesium; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; hydrazine; In tetrahydrofuran; ethanol; dichloromethane; acetone; toluene;

DOI:10.1021/jm00368a003

upstream raw materials:

5-<2-<2-<4-(benzyloxy)phenyl>-1(S)-<<(2,2,2-trichloroethyloxy)carbonyl>amino>ethyl>-1,3-dioxolan-2-yl>-3-oxopentanoyl-L-phenylalanyl-L-leucine methyl ester

(S)-N^α-phthaloyl-O-benzyltyrosine

(S)-N^α-phthaloyl-O-benzyltyrosine chloride

2-<2-<4-(benzyloxy)phenyl>-1(S)-phthalimidoethyl>-2-(3-oxopropyl)-1,3-dioxolane

Downstream raw materials:

8(S)-amino-4,7-dioxo-9-(4-hydroxyphenyl)nonanoyl-L-phenylalanyl-L-leucine

4,7-dioxo-9-(4-hydroxyphenyl)-8(S)-<<(2,2,2-trichloroethoxy)carbonyl>amino>nonanoyl-L-phenylalanyl-L-leucine

5-<2-<2-(4-hydroxyphenyl)-1(S)-<<(2,2,2-trichloroethoxy)carbonyl>amino>ethyl>-1,3-dioxolan-2-yl>-3-oxopentanoyl-L-phenylalanyl-L-leucine

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