3(S)-<1(R)-hydroxyethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one

Base Information

Chemical Name:3(S)-<1(R)-hydroxyethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one
CAS No.:99827-43-7
Molecular Formula:C₁₉H₂₅NO₈S
Molecular Weight:427.475
Hs Code.:

Synonyms:3(S)-<1(R)-hydroxyethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one

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Chemical Property of 3(S)-<1(R)-hydroxyethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one

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Technology Process of 3(S)-<1(R)-hydroxyethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one

There total 7 articles about 3(S)-<1(R)-hydroxyethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one 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: 94.8%

: 99765-24-9
3(S)-<1(R)-<<(phenoxymethyl)carbonyl>oxy>ethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one

: 99827-43-7
3(S)-<1(R)-hydroxyethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one

Guidance literature:: With sodium methylate; In tetrahydrofuran; methanol; at -3 ℃; for 1h;
DOI:10.1021/jo00353a025

Reference yield:

: 98114-06-8
6α-Bromopenicillanic acid 1,1-dioxide methyl ester

: 99827-43-7
3(S)-<1(R)-hydroxyethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) DBU, 2.) CF₃COOH / tetrahydrofuran / 1.) 5 deg C, 1 h, 2.) 5 deg C, 5 min

2: tetrahydrofuran / Ambient temperature

3: 94 percent / K₂CO₃ / acetone / 2.5 h / Ambient temperature

4: 1.) LiCuBu / 1.) THF, -78 deg C, 40 min, 2.) THF, -78 deg C, 1 h

5: 59.3 percent / triphenylphosphine, diethyl azocarboxylate / tetrahydrofuran / 0 - 8 °C

6: 94.8 percent / CH₃ONa / tetrahydrofuran; methanol / 1 h / -3 °C

With sodium methylate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; acetone;
DOI:10.1021/jo00353a025

Reference yield:

: 2-((3S,4R)-3-Bromo-2-oxo-4-sulfino-azetidin-1-yl)-3-methyl-but-2-enoic acid methyl ester

: 99827-43-7
3(S)-<1(R)-hydroxyethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: tetrahydrofuran / Ambient temperature

2: 94 percent / K₂CO₃ / acetone / 2.5 h / Ambient temperature

3: 1.) LiCuBu / 1.) THF, -78 deg C, 40 min, 2.) THF, -78 deg C, 1 h

4: 59.3 percent / triphenylphosphine, diethyl azocarboxylate / tetrahydrofuran / 0 - 8 °C

5: 94.8 percent / CH₃ONa / tetrahydrofuran; methanol / 1 h / -3 °C

With sodium methylate; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; acetone;
DOI:10.1021/jo00353a025