Acetic acid (2S,3R)-1-benzyl-2-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-4-oxo-azetidin-3-yl ester

Base Information

Chemical Name:Acetic acid (2S,3R)-1-benzyl-2-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-4-oxo-azetidin-3-yl ester
CAS No.:260354-42-5
Molecular Formula:C₂₄H₂₇NO₆
Molecular Weight:425.481
Hs Code.:

Synonyms:Acetic acid (2S,3R)-1-benzyl-2-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-4-oxo-azetidin-3-yl ester

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Chemical Property of Acetic acid (2S,3R)-1-benzyl-2-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-4-oxo-azetidin-3-yl ester

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Technology Process of Acetic acid (2S,3R)-1-benzyl-2-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-4-oxo-azetidin-3-yl ester

There total 5 articles about Acetic acid (2S,3R)-1-benzyl-2-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-4-oxo-azetidin-3-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:

: 3901-07-3
3-(4-methoxy-phenyl)acrylic acid methyl ester

: 260354-42-5
Acetic acid (2S,3R)-1-benzyl-2-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-4-oxo-azetidin-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / K₂OsO₂(OH)4; (DHQ)2-PHAL; K₃Fe(CN)6 / K₂CO₃; methanesulfonamide / H₂O; 2-methyl-propan-2-ol / 20 °C

2: 85 percent / p-TsOH*H₂O / benzene / 1 h / Heating

3: DIBAL / toluene / 2 h / -78 °C

4: CH₂Cl₂ / 1 h / 0 °C

5: 5.11 g / Et₃N / CH₂Cl₂ / 20 °C

With potassium dioxotetrahydroxoosmate(VI); (DHQ)2-PHAL; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; potassium hexacyanoferrate(III); methanesulfonamide; potassium carbonate; In dichloromethane; water; toluene; tert-butyl alcohol; benzene; 1: Sharpless AD reaction / 2: Cycloaddition / 3: Reduction / 4: Condensation / 5: Cycloaddition;
DOI:10.1021/jo990964c

Reference yield:

: 1025887-95-9
Benzyl-[1-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-meth-(E)-ylidene]-amine

: 13831-31-7
Acetoxyacetyl chloride

: 260354-42-5
Acetic acid (2S,3R)-1-benzyl-2-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-4-oxo-azetidin-3-yl ester

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃;
DOI:10.1021/jo990964c

Reference yield:

: 122517-81-1
(2R,3S)-methyl 2,3-dihydroxy-3-(4-methoxyphenyl)propanoate

: 260354-42-5
Acetic acid (2S,3R)-1-benzyl-2-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-4-oxo-azetidin-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / p-TsOH*H₂O / benzene / 1 h / Heating

2: DIBAL / toluene / 2 h / -78 °C

3: CH₂Cl₂ / 1 h / 0 °C

4: 5.11 g / Et₃N / CH₂Cl₂ / 20 °C

With diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; In dichloromethane; toluene; benzene; 1: Cycloaddition / 2: Reduction / 3: Condensation / 4: Cycloaddition;
DOI:10.1021/jo990964c