(6S,9S,12S)-6-benzyl-15-methoxy-12-(methylamino)-9-[(1S)-1-methylpropyl]-4,7,10-triazabicyclo[12.3.1]octadeca-1(18),2,14,16-tetraene-5,8,11-trione

Base Information

• Chemical Name: (6S,9S,12S)-6-benzyl-15-methoxy-12-(methylamino)-9-[(1S)-1-methylpropyl]-4,7,10-triazabicyclo[12.3.1]octadeca-1(18),2,14,16-tetraene-5,8,11-trione
• CAS No.: 38840-26-5
• Molecular Formula: C₂₈H₃₆N₄O₄
• Molecular Weight: 492.618
• Mol file: 38840-26-5.mol

Synonyms:Mucronine B;

Chemical Property of (6S,9S,12S)-6-benzyl-15-methoxy-12-(methylamino)-9-[(1S)-1-methylpropyl]-4,7,10-triazabicyclo[12.3.1]octadeca-1(18),2,14,16-tetraene-5,8,11-trione

Chemical Property:

• Vapor Pressure: 9.94E-27mmHg at 25°C
• Melting Point: 222-4°C
• Boiling Point: 816.2°Cat760mmHg
• Flash Point: 447.4°C
• PSA: 119.03000
• Density: 1.19g/cm³
• LogP: 3.40320

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: A further peptide alkaloid obtained from the bark of Zizyphus mucro nata Willd.,this base also furnishes colourless needles from Me2CO-light petroleum. It is, however, dextrorotatory having [o:lbs + 1750 (c 0.2, CHCI3). The ultraviolet spectrum exhibits one absorption maximum at 277 mil in EtOH solution.

Technology Process of (6S,9S,12S)-6-benzyl-15-methoxy-12-(methylamino)-9-[(1S)-1-methylpropyl]-4,7,10-triazabicyclo[12.3.1]octadeca-1(18),2,14,16-tetraene-5,8,11-trione

There total 22 articles about (6S,9S,12S)-6-benzyl-15-methoxy-12-(methylamino)-9-[(1S)-1-methylpropyl]-4,7,10-triazabicyclo[12.3.1]octadeca-1(18),2,14,16-tetraene-5,8,11-trione 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:

H-(S)-Ile-(S)-Phe-OCH3 (54793-60-1) → Mucronin B (38840-26-5,84173-39-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) NaOH, 2) DCCD / 1) H₂O/dioxane, r.t., 4h, 2) CH₂Cl₂, 0 deg C, 10h

2: NaOH / H₂O; dioxane / 4 h / Ambient temperature

3: DCCD / CH₂Cl₂ / 10 h / 0 °C

4: 85 percent / H₂ / Pd / dioxane / 5 h / 95 °C

5: pyridine / 20 h / Ambient temperature

6: trifluoroacetic acid / 20 h / 50 °C

7: NaIO₄ / tetrahydrofuran; methanol; H₂O / 0.5 h / Ambient temperature

With sodium hydroxide; sodium periodate; hydrogen; dicyclohexyl-carbodiimide; palladium; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; water; trifluoroacetic acid;

Reference yield:

(S)-2-{(2S,3S)-2-[3-[5-(2-Benzyloxycarbonylamino-1-hydroxy-ethyl)-2-methoxy-phenyl]-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-3-methyl-pentanoylamino}-3-phenyl-propionic acid (84133-16-4) → Mucronin B (38840-26-5,84173-39-7)

Guidance literature:

Multi-step reaction with 5 steps

1: DCCD / CH₂Cl₂ / 10 h / 0 °C

2: 85 percent / H₂ / Pd / dioxane / 5 h / 95 °C

3: pyridine / 20 h / Ambient temperature

4: trifluoroacetic acid / 20 h / 50 °C

5: NaIO₄ / tetrahydrofuran; methanol; H₂O / 0.5 h / Ambient temperature

With sodium periodate; hydrogen; dicyclohexyl-carbodiimide; palladium; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; water; trifluoroacetic acid;

Reference yield:

(S)-2-{(2S,3S)-2-[3-[5-(2-Benzyloxycarbonylamino-1-hydroxy-ethyl)-2-methoxy-phenyl]-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-3-methyl-pentanoylamino}-3-phenyl-propionic acid pentafluorophenyl ester (84133-17-5) → Mucronin B (38840-26-5,84173-39-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / H₂ / Pd / dioxane / 5 h / 95 °C

2: pyridine / 20 h / Ambient temperature

3: trifluoroacetic acid / 20 h / 50 °C

4: NaIO₄ / tetrahydrofuran; methanol; H₂O / 0.5 h / Ambient temperature

With sodium periodate; hydrogen; palladium; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; water; trifluoroacetic acid;

upstream raw materials:

(2RS,6S,9S,12S)-2-Acetoxy-12-<(tert-butyloxycarbonyl)(methyl)amino>-15-methoxy-9-(1-methylpropyl)-6-phenylmethyl-4,7,10-triazabicyclo<12.3.1>octadeca-1(18),14,16-trien-5,8,11-trion

H-(S)-Ile-(S)-Phe-OCH₃

Acetic acid (6S,9S)-6-benzyl-12-(tert-butoxycarbonyl-methyl-amino)-9-((S)-sec-butyl)-15-methoxy-5,8,11-trioxo-4,7,10-triaza-bicyclo[12.3.1]octadeca-1⁽¹⁸⁾,14,16-trien-2-yl ester

(S)-2-{(2S,3S)-2-[3-[5-(2-Benzyloxycarbonylamino-1-hydroxy-ethyl)-2-methoxy-phenyl]-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-3-methyl-pentanoylamino}-3-phenyl-propionic acid

Refernces

• 1、 Schmidt, Ulrich,Schanbacher, Ute. "Totalsynthese des Mucronins B". . p. 150 - 151. Retrieved 2007/10/02.