3-Methoxy-5-methyl-naphthalene-1-carboxylic acid (S)-[([(3R,4R,5S)-3,4-bis-benzyloxy-5-methanesulfonyloxymethyl-pyrrolidin-(2E)-ylidene]-{1-[1-methoxy-meth-(Z)-ylidene]-2-oxo-propylcarbamoyl}-methyl)-carbamoyl]-((S)-2-methyl-oxiranyl)-methyl ester

Base Information

• Chemical Name: 3-Methoxy-5-methyl-naphthalene-1-carboxylic acid (S)-[([(3R,4R,5S)-3,4-bis-benzyloxy-5-methanesulfonyloxymethyl-pyrrolidin-(2E)-ylidene]-{1-[1-methoxy-meth-(Z)-ylidene]-2-oxo-propylcarbamoyl}-methyl)-carbamoyl]-((S)-2-methyl-oxiranyl)-methyl ester
• CAS No.: 205442-01-9
• Molecular Formula: C₄₅H₄₉N₃O₁₃S
• Molecular Weight: 871.962

Synonyms:3-Methoxy-5-methyl-naphthalene-1-carboxylic acid (S)-[([(3R,4R,5S)-3,4-bis-benzyloxy-5-methanesulfonyloxymethyl-pyrrolidin-(2E)-ylidene]-{1-[1-methoxy-meth-(Z)-ylidene]-2-oxo-propylcarbamoyl}-methyl)-carbamoyl]-((S)-2-methyl-oxiranyl)-methyl ester

Chemical Property of 3-Methoxy-5-methyl-naphthalene-1-carboxylic acid (S)-[([(3R,4R,5S)-3,4-bis-benzyloxy-5-methanesulfonyloxymethyl-pyrrolidin-(2E)-ylidene]-{1-[1-methoxy-meth-(Z)-ylidene]-2-oxo-propylcarbamoyl}-methyl)-carbamoyl]-((S)-2-methyl-oxiranyl)-methyl ester

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Technology Process of 3-Methoxy-5-methyl-naphthalene-1-carboxylic acid (S)-[([(3R,4R,5S)-3,4-bis-benzyloxy-5-methanesulfonyloxymethyl-pyrrolidin-(2E)-ylidene]-{1-[1-methoxy-meth-(Z)-ylidene]-2-oxo-propylcarbamoyl}-methyl)-carbamoyl]-((S)-2-methyl-oxiranyl)-methyl ester

There total 29 articles about 3-Methoxy-5-methyl-naphthalene-1-carboxylic acid (S)-[([(3R,4R,5S)-3,4-bis-benzyloxy-5-methanesulfonyloxymethyl-pyrrolidin-(2E)-ylidene]-{1-[1-methoxy-meth-(Z)-ylidene]-2-oxo-propylcarbamoyl}-methyl)-carbamoyl]-((S)-2-methyl-oxiranyl)-methyl 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:

diazomethane (186581-53-3,908094-01-9,334-88-3) + 3-methoxy-5-methyl-naphthalene-1-carboxylic acid {[[1-acetyl-2-(tert-butyl-dimethyl-silanyloxy)-2-cyano-ethylcarbamoyl]-(3,4-bis-benzyloxy-5-methanesulfonyloxymethyl-pyrrolidin-2-ylidene)-methyl]-carbamoyl}-(2-methyl-oxiranyl)-methyl ester (205442-00-8) → 3-Methoxy-5-methyl-naphthalene-1-carboxylic acid (S)-[([(3R,4R,5S)-3,4-bis-benzyloxy-5-methanesulfonyloxymethyl-pyrrolidin-(2E)-ylidene]-{1-[1-methoxy-meth-(Z)-ylidene]-2-oxo-propylcarbamoyl}-methyl)-carbamoyl]-((S)-2-methyl-oxiranyl)-methyl ester (205442-01-9)

Guidance literature:

3-methoxy-5-methyl-naphthalene-1-carboxylic acid {[[1-acetyl-2-(tert-butyl-dimethyl-silanyloxy)-2-cyano-ethylcarbamoyl]-(3,4-bis-benzyloxy-5-methanesulfonyloxymethyl-pyrrolidin-2-ylidene)-methyl]-carbamoyl}-(2-methyl-oxiranyl)-methyl ester; With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 3h;

With sodium hydrogencarbonate; In tetrahydrofuran; at 20 ℃; for 0.166667h;

diazomethane; In diethyl ether; dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/S0040-4020(03)00379-X

Reference yield:

(2S,3R,4R)-3,4-Bis-benzyloxy-2-methanesulfonyloxymethyl-5-[2-[(3-methoxy-5-methyl-naphthalene-1-carbonyloxy)-((S)-2-methyl-oxiranyl)-methyl]-5-oxo-oxazol-(4E)-ylidene]-pyrrolidine-1-carboxylic acid allyl ester → 3-Methoxy-5-methyl-naphthalene-1-carboxylic acid (S)-[([(3R,4R,5S)-3,4-bis-benzyloxy-5-methanesulfonyloxymethyl-pyrrolidin-(2E)-ylidene]-{1-[1-methoxy-meth-(Z)-ylidene]-2-oxo-propylcarbamoyl}-methyl)-carbamoyl]-((S)-2-methyl-oxiranyl)-methyl ester (205442-01-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 78 percent / tetrahydrofuran / 0.67 h / 50 °C / vacuum

2.1: 94 percent / DDQ / CH₂Cl₂ / 1 h / 20 °C

3.1: 98 percent / Dess-Martin reagent / CH₂Cl₂ / 1 h / 20 °C

4.1: 89 percent / PPh₃; Pd(PPh₃)4; AcOH / dimethylsulfoxide

5.1: TBAF; AcOH / tetrahydrofuran / 3 h / 20 °C

5.2: aq. NaHCO₃ / tetrahydrofuran / 0.17 h / 20 °C

5.3: 13.2 mg / CH₂Cl₂; diethyl ether / 1 h / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; Dess-Martin periodane; acetic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4020(03)00379-X

Reference yield:

4-[(3R,4R,5S)-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidin-2-ylidene]-2-[2,3-epoxy-1-(3-methoxy-5-methyl-1-naphthoyloxy)-2-methylpropyl]-4H-oxazol-5-one → 3-Methoxy-5-methyl-naphthalene-1-carboxylic acid (S)-[([(3R,4R,5S)-3,4-bis-benzyloxy-5-methanesulfonyloxymethyl-pyrrolidin-(2E)-ylidene]-{1-[1-methoxy-meth-(Z)-ylidene]-2-oxo-propylcarbamoyl}-methyl)-carbamoyl]-((S)-2-methyl-oxiranyl)-methyl ester (205442-01-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: DMAP / tetrahydrofuran / 0.17 h / 20 °C

2.1: 78 percent / tetrahydrofuran / 0.67 h / 50 °C / vacuum

3.1: 94 percent / DDQ / CH₂Cl₂ / 1 h / 20 °C

4.1: 98 percent / Dess-Martin reagent / CH₂Cl₂ / 1 h / 20 °C

5.1: 89 percent / PPh₃; Pd(PPh₃)4; AcOH / dimethylsulfoxide

6.1: TBAF; AcOH / tetrahydrofuran / 3 h / 20 °C

6.2: aq. NaHCO₃ / tetrahydrofuran / 0.17 h / 20 °C

6.3: 13.2 mg / CH₂Cl₂; diethyl ether / 1 h / 20 °C

With dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; Dess-Martin periodane; acetic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4020(03)00379-X

upstream raw materials:

diazomethane

3-methoxy-5-methyl-naphthalene-1-carboxylic acid {[[1-acetyl-2-(tert-butyl-dimethyl-silanyloxy)-2-cyano-ethylcarbamoyl]-(3,4-bis-benzyloxy-5-methanesulfonyloxymethyl-pyrrolidin-2-ylidene)-methyl]-carbamoyl}-(2-methyl-oxiranyl)-methyl ester

C₅₅H₆₆N₄O₁₅SSi

C₅₅H₆₈N₄O₁₅SSi

Downstream raw materials:

13-desacetyl-12,13-di-O-benzyloxy-4-O-methyl-carzinophilin

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