(3R,4S)-1-(tert-butoxycarbonyl)-3-triethylsilyloxy-4-(3-triethylsilyloxymethyl)phenylazetidin-2-one

Base Information

Chemical Name:(3R,4S)-1-(tert-butoxycarbonyl)-3-triethylsilyloxy-4-(3-triethylsilyloxymethyl)phenylazetidin-2-one
CAS No.:1431704-54-9
Molecular Formula:C₂₇H₄₇NO₅Si₂
Molecular Weight:521.845
Hs Code.:

Synonyms:(3R,4S)-1-(tert-butoxycarbonyl)-3-triethylsilyloxy-4-(3-triethylsilyloxymethyl)phenylazetidin-2-one

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Chemical Property of (3R,4S)-1-(tert-butoxycarbonyl)-3-triethylsilyloxy-4-(3-triethylsilyloxymethyl)phenylazetidin-2-one

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Technology Process of (3R,4S)-1-(tert-butoxycarbonyl)-3-triethylsilyloxy-4-(3-triethylsilyloxymethyl)phenylazetidin-2-one

There total 10 articles about (3R,4S)-1-(tert-butoxycarbonyl)-3-triethylsilyloxy-4-(3-triethylsilyloxymethyl)phenylazetidin-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: 86.5%

: 24424-99-5
di-tert-butyl dicarbonate

: 1431704-53-8
(3R,4S)-3-triethylsilyloxy-4-(3-triethylsilyloxymethyl)phenylazetidin-2-one

: 1431704-54-9
(3R,4S)-1-(tert-butoxycarbonyl)-3-triethylsilyloxy-4-(3-triethylsilyloxymethyl)phenylazetidin-2-one

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1039/c3ob40407b

Reference yield:

: 52010-98-7
3-(hydroxymethyl)benzaldehyde

: 1431704-54-9
(3R,4S)-1-(tert-butoxycarbonyl)-3-triethylsilyloxy-4-(3-triethylsilyloxymethyl)phenylazetidin-2-one

Guidance literature:: Multi-step reaction with 9 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C

2: sodium sulfate / dichloromethane / 12 h / 20 °C

3: triethylamine / dichloromethane / 20 h / 20 °C

4: water; ammonium cerium (IV) nitrate / acetonitrile / 0.25 h / -15 - -10 °C

5: pyridinium p-toluenesulfonate / tert-butyl alcohol / 4 h / Inert atmosphere; Reflux

6: lipase from pig liver / diethyl ether; aq. phosphate buffer / 1.17 h / 24 °C / pH 7.5 / Enzymatic reaction

7: pyridine; pyrrolidine / tetrahydrofuran / 7 h / 20 °C

8: pyridine / tetrahydrofuran / 8 h / 20 °C

9: triethylamine; dmap / dichloromethane / 12 h / 20 °C

With pyrrolidine; pyridine; dmap; ammonium cerium (IV) nitrate; lipase from pig liver; water; pyridinium p-toluenesulfonate; sodium sulfate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; aq. phosphate buffer; diethyl ether; dichloromethane; acetonitrile; tert-butyl alcohol;
DOI:10.1039/c3ob40407b

Reference yield:

: 186246-13-9
3-(((2-methoxyethoxy)methoxy)methyl)benzaldehyde

: 1431704-54-9
(3R,4S)-1-(tert-butoxycarbonyl)-3-triethylsilyloxy-4-(3-triethylsilyloxymethyl)phenylazetidin-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: sodium sulfate / dichloromethane / 12 h / 20 °C

2: triethylamine / dichloromethane / 20 h / 20 °C

3: water; ammonium cerium (IV) nitrate / acetonitrile / 0.25 h / -15 - -10 °C

4: pyridinium p-toluenesulfonate / tert-butyl alcohol / 4 h / Inert atmosphere; Reflux

5: lipase from pig liver / diethyl ether; aq. phosphate buffer / 1.17 h / 24 °C / pH 7.5 / Enzymatic reaction

6: pyridine; pyrrolidine / tetrahydrofuran / 7 h / 20 °C

7: pyridine / tetrahydrofuran / 8 h / 20 °C

8: triethylamine; dmap / dichloromethane / 12 h / 20 °C

With pyrrolidine; pyridine; dmap; ammonium cerium (IV) nitrate; lipase from pig liver; water; pyridinium p-toluenesulfonate; sodium sulfate; triethylamine; In tetrahydrofuran; aq. phosphate buffer; diethyl ether; dichloromethane; acetonitrile; tert-butyl alcohol;
DOI:10.1039/c3ob40407b