3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>azetidin-2-one

Base Information

Chemical Name:3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>azetidin-2-one
CAS No.:99765-26-1
Molecular Formula:C₁₉H₃₁NO₆SSi
Molecular Weight:429.61
Hs Code.:

Synonyms:3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>azetidin-2-one

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Chemical Property of 3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>azetidin-2-one

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Technology Process of 3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>azetidin-2-one

There total 6 articles about 3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>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: 58.7%

: 99765-25-0
3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one

: 99765-26-1
3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>azetidin-2-one

Guidance literature:: With potassium permanganate; acetic acid; In water; acetone; for 24h;
DOI:10.1021/jo00353a025

Reference yield:

: 99765-22-7
3(S)-bromo-4(R)-<(2,5-dihydroxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one

: 99765-26-1
3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>azetidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / K₂CO₃ / acetone / 2.5 h / Ambient temperature

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

3: 59.3 percent / triphenylphosphine, diethyl azocarboxylate / tetrahydrofuran / 0 - 8 °C

4: 94.8 percent / CH₃ONa / tetrahydrofuran; methanol / 1 h / -3 °C

5: 98 percent / 4-(dimethylamino)pyridine / dimethylformamide / Ambient temperature

6: 58.7 percent / acetic acid, KMnO₄ / acetone; H₂O / 24 h

With dmap; potassium permanganate; sodium methylate; potassium carbonate; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00353a025

Reference yield:

: 99765-23-8
3(S)-bromo-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one

: 99765-26-1
3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>azetidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

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

2: 59.3 percent / triphenylphosphine, diethyl azocarboxylate / tetrahydrofuran / 0 - 8 °C

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

4: 98 percent / 4-(dimethylamino)pyridine / dimethylformamide / Ambient temperature

5: 58.7 percent / acetic acid, KMnO₄ / acetone; H₂O / 24 h

With dmap; potassium permanganate; sodium methylate; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00353a025