(1S,8R,8aR)-8-benzyloxy-1-(tert-butyldimethylsilyloxy)-2,3,8,8a-tetrahydroindolizin-5(1H)-one

Base Information

Chemical Name:(1S,8R,8aR)-8-benzyloxy-1-(tert-butyldimethylsilyloxy)-2,3,8,8a-tetrahydroindolizin-5(1H)-one
CAS No.:1257423-95-2
Molecular Formula:C₂₁H₃₁NO₃Si
Molecular Weight:373.568
Hs Code.:

Synonyms:

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Chemical Property of (1S,8R,8aR)-8-benzyloxy-1-(tert-butyldimethylsilyloxy)-2,3,8,8a-tetrahydroindolizin-5(1H)-one

Chemical Property:

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Technology Process of (1S,8R,8aR)-8-benzyloxy-1-(tert-butyldimethylsilyloxy)-2,3,8,8a-tetrahydroindolizin-5(1H)-one

There total 6 articles about (1S,8R,8aR)-8-benzyloxy-1-(tert-butyldimethylsilyloxy)-2,3,8,8a-tetrahydroindolizin-5(1H)-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:

: C₂₇H₃₇NO₃SeSi

: 1257423-95-2
(1S,8R,8aR)-8-benzyloxy-1-(tert-butyldimethylsilyloxy)-2,3,8,8a-tetrahydroindolizin-5(1H)-one

Guidance literature:: With dihydrogen peroxide; acetic acid; In tetrahydrofuran; at 0 ℃;
DOI:10.1007/s11426-010-4065-1

Reference yield:

: 130403-91-7
(3S)-3-[tert-butyl(dimethyl)silyl]oxypyrrolidin-2-one

: 1257423-95-2
(1S,8R,8aR)-8-benzyloxy-1-(tert-butyldimethylsilyloxy)-2,3,8,8a-tetrahydroindolizin-5(1H)-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / -20 - 0 °C / Inert atmosphere

1.2: 1 h / 0 °C / Inert atmosphere

2.1: sodium tetrahydroborate / methanol / 0.25 h / -20 °C

3.1: pyridinium p-toluenesulfonate; toluene-4-sulfonic acid / dichloromethane / 24 h / 20 °C

4.1: samarium diiodide / tetrahydrofuran / 0.17 h / Cooling with ice

5.1: 10% palladium on activated carbon; hydrogen; triethylamine / methanol / 20 °C

6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

6.2: 0 - 45 °C / Inert atmosphere

7.1: lithium diisopropyl amide / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

7.2: 3 h / -78 °C / Inert atmosphere

8.1: dihydrogen peroxide; acetic acid / tetrahydrofuran / 0 °C

With sodium tetrahydroborate; samarium diiodide; 10% palladium on activated carbon; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; mineral oil;
DOI:10.1007/s11426-010-4065-1

Reference yield:

: 1257423-97-4
(1S,8R,8aR)-1-(tert-butyldimethylsilyloxy)-8-hydroxy-5-indolizidinone

: 1257423-95-2
(1S,8R,8aR)-8-benzyloxy-1-(tert-butyldimethylsilyloxy)-2,3,8,8a-tetrahydroindolizin-5(1H)-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

1.2: 0 - 45 °C / Inert atmosphere

2.1: lithium diisopropyl amide / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

2.2: 3 h / -78 °C / Inert atmosphere

3.1: dihydrogen peroxide; acetic acid / tetrahydrofuran / 0 °C

With dihydrogen peroxide; sodium hydride; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; mineral oil;
DOI:10.1007/s11426-010-4065-1