{(2R,3S)-2-[(1R,3S)-3-(Benzyloxycarbonyl-methyl-amino)-2-oxo-cyclohexyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 9H-fluoren-9-yl ester

Base Information

• Chemical Name: {(2R,3S)-2-[(1R,3S)-3-(Benzyloxycarbonyl-methyl-amino)-2-oxo-cyclohexyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 9H-fluoren-9-yl ester
• CAS No.: 300568-75-6
• Molecular Formula: C₄₁H₄₈N₂O₈Si
• Molecular Weight: 724.926
• Mol file: 300568-75-6.mol

Synonyms:{(2R,3S)-2-[(1R,3S)-3-(Benzyloxycarbonyl-methyl-amino)-2-oxo-cyclohexyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 9H-fluoren-9-yl ester

Chemical Property of {(2R,3S)-2-[(1R,3S)-3-(Benzyloxycarbonyl-methyl-amino)-2-oxo-cyclohexyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 9H-fluoren-9-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(2R,3S)-2-[(1R,3S)-3-(Benzyloxycarbonyl-methyl-amino)-2-oxo-cyclohexyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 9H-fluoren-9-yl ester

There total 7 articles about {(2R,3S)-2-[(1R,3S)-3-(Benzyloxycarbonyl-methyl-amino)-2-oxo-cyclohexyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 9H-fluoren-9-yl 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: 94.6%

((1S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohexyl)-methyl-carbamic acid benzyl ester (185675-65-4) + fluorenyloxalyl chloride (300568-84-7) → {(2R,3S)-2-[(1R,3S)-3-(Benzyloxycarbonyl-methyl-amino)-2-oxo-cyclohexyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 9H-fluoren-9-yl ester (300568-75-6)

Guidance literature:

With pyridine; potassium carbonate; In dichloromethane; at 0 - 25 ℃;

DOI:10.1016/S0040-4020(00)00414-2

Reference yield:

9-Fluorenol (1689-64-1) → {(2R,3S)-2-[(1R,3S)-3-(Benzyloxycarbonyl-methyl-amino)-2-oxo-cyclohexyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 9H-fluoren-9-yl ester (300568-75-6)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 1.5 h / 0 °C

2: 94.6 percent / potassium carbonate; pyridine / CH₂Cl₂ / 0 - 25 °C

With pyridine; potassium carbonate; In tetrahydrofuran; dichloromethane; 1: Substitution / 2: Acylation;

DOI:10.1016/S0040-4020(00)00414-2

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → {(2R,3S)-2-[(1R,3S)-3-(Benzyloxycarbonyl-methyl-amino)-2-oxo-cyclohexyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 9H-fluoren-9-yl ester (300568-75-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / diisopropylamine / CH₂Cl₂ / 2 h / 0 °C

2: 79 percent / oxalyl chloride; dimethyl sulfoxide / CH₂Cl₂ / 1 h / -70 °C

3: 94.6 percent / potassium carbonate; pyridine / CH₂Cl₂ / 0 - 25 °C

With pyridine; oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; diisopropylamine; In dichloromethane; 1: Acylation / 2: Oxidation / 3: Acylation;

DOI:10.1016/S0040-4020(00)00414-2

upstream raw materials:

((1S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohexyl)-methyl-carbamic acid benzyl ester

fluorenyloxalyl chloride

9-Fluorenol

benzyl chloroformate

Downstream raw materials:

(1S,5S,8aS,8bR)-5-(Benzyloxycarbonyl-methyl-amino)-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 9H-fluoren-9-yl ester

GV129606

5-(benzyloxycarbonyl-methyl-amino)-1-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 9H-fluoren-9-yl ester