(1R,9S)-12-[1-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-meth-(Z)-ylidene]-3-hydroxy-4,6-dimethoxy-5-methyl-10-oxo-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-13-carboxylic acid benzyl ester

Base Information

• Chemical Name: (1R,9S)-12-[1-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-meth-(Z)-ylidene]-3-hydroxy-4,6-dimethoxy-5-methyl-10-oxo-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-13-carboxylic acid benzyl ester
• CAS No.: 127103-55-3
• Molecular Formula: C₃₉H₄₀N₂O₉
• Molecular Weight: 680.755

Synonyms:(1R,9S)-12-[1-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-meth-(Z)-ylidene]-3-hydroxy-4,6-dimethoxy-5-methyl-10-oxo-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-13-carboxylic acid benzyl ester

Chemical Property of (1R,9S)-12-[1-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-meth-(Z)-ylidene]-3-hydroxy-4,6-dimethoxy-5-methyl-10-oxo-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-13-carboxylic acid benzyl ester

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Technology Process of (1R,9S)-12-[1-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-meth-(Z)-ylidene]-3-hydroxy-4,6-dimethoxy-5-methyl-10-oxo-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-13-carboxylic acid benzyl ester

There total 6 articles about (1R,9S)-12-[1-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-meth-(Z)-ylidene]-3-hydroxy-4,6-dimethoxy-5-methyl-10-oxo-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-13-carboxylic acid benzyl ester 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:

5-(benzyloxy)-2,4-dimethoxy-3-methylbenzaldehyde (82622-02-4) → (1R,9S)-12-[1-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-meth-(Z)-ylidene]-3-hydroxy-4,6-dimethoxy-5-methyl-10-oxo-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid benzyl ester (127103-55-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 86 percent / t-BuOK, t-BuOH / tetrahydrofuran / 0 °C

2: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 80 °C / 51714.8 Torr

3: Et₃N / CH₂Cl₂ / Heating

4: Et₃N, DMAP / CH₂Cl₂ / -15 °C

5: 1.) t-BuOK, t-BuOH, 2.) DBU / 1.) THF, -78 deg C, 2.) 0 deg C

With dmap; potassium tert-butylate; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; tert-butyl alcohol; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1021/ja00165a095

Reference yield:

1-Acetyl-3-[1-(5-benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-meth-(Z)-ylidene]-piperazine-2,5-dione (127103-51-9) → (1R,9S)-12-[1-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-meth-(Z)-ylidene]-3-hydroxy-4,6-dimethoxy-5-methyl-10-oxo-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid benzyl ester (127103-55-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 80 °C / 51714.8 Torr

2: Et₃N / CH₂Cl₂ / Heating

3: Et₃N, DMAP / CH₂Cl₂ / -15 °C

4: 1.) t-BuOK, t-BuOH, 2.) DBU / 1.) THF, -78 deg C, 2.) 0 deg C

With dmap; potassium tert-butylate; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; tert-butyl alcohol; palladium on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1021/ja00165a095

Reference yield:

1-Acetyl-3-(5-hydroxy-2,4-dimethoxy-3-methyl-benzyl)-piperazine-2,5-dione (127103-52-0) → (1R,9S)-12-[1-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-meth-(Z)-ylidene]-3-hydroxy-4,6-dimethoxy-5-methyl-10-oxo-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid benzyl ester (127103-55-3)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N / CH₂Cl₂ / Heating

2: Et₃N, DMAP / CH₂Cl₂ / -15 °C

3: 1.) t-BuOK, t-BuOH, 2.) DBU / 1.) THF, -78 deg C, 2.) 0 deg C

With dmap; potassium tert-butylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; tert-butyl alcohol; In dichloromethane;

DOI:10.1021/ja00165a095

upstream raw materials:

3-[1-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-meth-(Z)-ylidene]-6-[5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-2,5-dioxo-piperazine-1-carboxylic acid benzyl ester

5-(benzyloxy)-2,4-dimethoxy-3-methylbenzaldehyde

1-Acetyl-3-(5-hydroxy-2,4-dimethoxy-3-methyl-benzyl)-piperazine-2,5-dione

1-Acetyl-3-[1-(5-benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-meth-(Z)-ylidene]-piperazine-2,5-dione

Downstream raw materials:

Carbonic acid (1S,3R)-1-[(R)-1-tert-butoxycarbonylamino-2-(5-tert-butoxycarbonyloxy-2,4-dimethoxy-3-methyl-phenyl)-ethyl]-3-hydroxymethyl-5,7-dimethoxy-2,6-dimethyl-1,2,3,4-tetrahydro-isoquinolin-8-yl ester tert-butyl ester

(+/-)-Saframycin A

(1S,9R,12R)-3-Hydroxy-12-(5-hydroxy-2,4-dimethoxy-3-methyl-benzyl)-4,6-dimethoxy-5,13-dimethyl-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-trien-10-one

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