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]-, methyl ester, (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]-, methyl ester, (S)-
• CAS No.: 88036-21-9
• Molecular Formula: C43H52Cl3N3O10
• Molecular Weight: 877.259

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]-, methyl ester, (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]-, methyl ester, (S)-

There total 9 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]-, methyl ester, (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: 55.9%

L-phenylalanyl-L-leucine methyl ester (38155-19-0) + 2-<2-<4-(benzyloxy)phenyl>-1(S)-<<(2,2,2-trichloroethoxy)carbonyl>amino>ethyl>-2-(5-carboxy-5-oxopentyl)-1,3-dioxolane (88036-20-8) → 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)

Guidance literature:

With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; for 64h; Ambient temperature;

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-trichloroethyloxy)carbonyl>amino>ethyl>-1,3-dioxolan-2-yl>-3-oxopentanoyl-L-phenylalanyl-L-leucine methyl ester (88036-21-9)

Guidance literature:

Multi-step reaction with 9 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

With chromium(VI) oxide; phosphorus pentachloride; sulfuric acid; benzotriazol-1-ol; toluene-4-sulfonic acid; magnesium; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; hydrazine; In 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-trichloroethyloxy)carbonyl>amino>ethyl>-1,3-dioxolan-2-yl>-3-oxopentanoyl-L-phenylalanyl-L-leucine methyl ester (88036-21-9)

Guidance literature:

Multi-step reaction with 8 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

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

DOI:10.1021/jm00368a003

upstream raw materials:

L-phenylalanyl-L-leucine methyl ester

2-<2-<4-(benzyloxy)phenyl>-1(S)-<<(2,2,2-trichloroethoxy)carbonyl>amino>ethyl>-2-(5-carboxy-5-oxopentyl)-1,3-dioxolane

(S)-N^α-phthaloyl-O-benzyltyrosine

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

Downstream raw materials:

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

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

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

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