Carbonic acid benzyl ester (R)-1-{(2R,3S)-1-[bis-(4-methoxy-phenyl)-methyl]-2-[1-methyl-2-(methyl-diphenyl-silanyloxy)-ethyl]-4-oxo-azetidin-3-yl}-ethyl ester

Base Information

• Chemical Name: Carbonic acid benzyl ester (R)-1-{(2R,3S)-1-[bis-(4-methoxy-phenyl)-methyl]-2-[1-methyl-2-(methyl-diphenyl-silanyloxy)-ethyl]-4-oxo-azetidin-3-yl}-ethyl ester
• CAS No.: 104362-94-9
• Molecular Formula: C₄₄H₄₇NO₇Si
• Molecular Weight: 729.945

Synonyms:

Chemical Property of Carbonic acid benzyl ester (R)-1-{(2R,3S)-1-[bis-(4-methoxy-phenyl)-methyl]-2-[1-methyl-2-(methyl-diphenyl-silanyloxy)-ethyl]-4-oxo-azetidin-3-yl}-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Carbonic acid benzyl ester (R)-1-{(2R,3S)-1-[bis-(4-methoxy-phenyl)-methyl]-2-[1-methyl-2-(methyl-diphenyl-silanyloxy)-ethyl]-4-oxo-azetidin-3-yl}-ethyl ester

There total 9 articles about Carbonic acid benzyl ester (R)-1-{(2R,3S)-1-[bis-(4-methoxy-phenyl)-methyl]-2-[1-methyl-2-(methyl-diphenyl-silanyloxy)-ethyl]-4-oxo-azetidin-3-yl}-ethyl 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: 90.0%

(3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-1-(di-p-anisylmethyl)-4-(1-diphenylmethylsilyloxymethylethenyl)-2-azetidinone (104380-28-1) → Carbonic acid benzyl ester (R)-1-{(2R,3S)-1-[bis-(4-methoxy-phenyl)-methyl]-2-[1-methyl-2-(methyl-diphenyl-silanyloxy)-ethyl]-4-oxo-azetidin-3-yl}-ethyl ester (104362-94-9,104420-06-6)

Guidance literature:

With hydrogen; platinum(IV) oxide; In acetonitrile; at 0 - 5 ℃; for 1.5h;

DOI:10.1248/cpb.40.1098

Reference yield:

(3S,4S)-4-carboxy-1-(di-p-anisylmethyl)-3-<(R)-1-hydroxyethyl>-2-azetidinone (86258-97-1) → Carbonic acid benzyl ester (R)-1-{(2R,3S)-1-[bis-(4-methoxy-phenyl)-methyl]-2-[1-methyl-2-(methyl-diphenyl-silanyloxy)-ethyl]-4-oxo-azetidin-3-yl}-ethyl ester (104362-94-9,104420-06-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / 98percent aq. H₂SO₄ / 3 h / 65 °C

2: 88 percent / tetrahydrofuran / 1 h / 0 - 5 °C

3: 100 percent / 4-dimethylaminopyridine (DMAP) / CH₂Cl₂ / 12 h / 0 - 20 °C

4: 89 percent / SOCl₂, pyridine / toluene / 5 h / 20 - 30 °C

5: 95 percent / Cl₂ / ethyl acetate; CCl₄ / 1 h / Ambient temperature

6: 79 percent / Cu₂O, p-toluenesulfonic acid monohydrate, water / dimethylsulfoxide / 2 h / 50 - 55 °C

7: 67 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

8: 90 percent / H₂ / PtO₂ / acetonitrile / 1.5 h / 0 - 5 °C

With pyridine; 1H-imidazole; copper(I) oxide; dmap; thionyl chloride; sulfuric acid; water; hydrogen; chlorine; toluene-4-sulfonic acid; platinum(IV) oxide; In tetrahydrofuran; tetrachloromethane; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1248/cpb.40.1098

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → Carbonic acid benzyl ester (R)-1-{(2R,3S)-1-[bis-(4-methoxy-phenyl)-methyl]-2-[1-methyl-2-(methyl-diphenyl-silanyloxy)-ethyl]-4-oxo-azetidin-3-yl}-ethyl ester (104362-94-9,104420-06-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / 4-dimethylaminopyridine (DMAP) / CH₂Cl₂ / 12 h / 0 - 20 °C

2: 89 percent / SOCl₂, pyridine / toluene / 5 h / 20 - 30 °C

3: 95 percent / Cl₂ / ethyl acetate; CCl₄ / 1 h / Ambient temperature

4: 79 percent / Cu₂O, p-toluenesulfonic acid monohydrate, water / dimethylsulfoxide / 2 h / 50 - 55 °C

5: 67 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

6: 90 percent / H₂ / PtO₂ / acetonitrile / 1.5 h / 0 - 5 °C

With pyridine; 1H-imidazole; copper(I) oxide; dmap; thionyl chloride; water; hydrogen; chlorine; toluene-4-sulfonic acid; platinum(IV) oxide; In tetrachloromethane; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1248/cpb.40.1098

upstream raw materials:

(3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-1-(di-p-anisylmethyl)-4-(1-diphenylmethylsilyloxymethylethenyl)-2-azetidinone

(3S,4S)-4-carboxy-1-(di-p-anisylmethyl)-3-<(R)-1-hydroxyethyl>-2-azetidinone

benzyl chloroformate

(3S,4S)-1-(di-p-anisylmethyl)-3-<(R)-1-hydroxyethyl>-4-(1-hydroxy-1-methylethyl)-2-azetidinone

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