(1S,8R,8aR)-8-benzyloxy-1-(tert-butyldimethylsilyloxy)-5-indolizidinone

Base Information

Chemical Name:(1S,8R,8aR)-8-benzyloxy-1-(tert-butyldimethylsilyloxy)-5-indolizidinone
CAS No.:1257424-01-3
Molecular Formula:C₂₁H₃₃NO₃Si
Molecular Weight:375.583
Hs Code.:

Synonyms:(1S,8R,8aR)-8-benzyloxy-1-(tert-butyldimethylsilyloxy)-5-indolizidinone

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1S,8R,8aR)-8-benzyloxy-1-(tert-butyldimethylsilyloxy)-5-indolizidinone

Chemical Property:

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Technology Process of (1S,8R,8aR)-8-benzyloxy-1-(tert-butyldimethylsilyloxy)-5-indolizidinone

There total 4 articles about (1S,8R,8aR)-8-benzyloxy-1-(tert-butyldimethylsilyloxy)-5-indolizidinone 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: 93.0%

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

: 100-39-0
benzyl bromide

: 1257424-01-3
(1S,8R,8aR)-8-benzyloxy-1-(tert-butyldimethylsilyloxy)-5-indolizidinone

Guidance literature:: (1S,8R,8aR)-1-(tert-butyldimethylsilyloxy)-8-hydroxy-5-indolizidinone; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

benzyl bromide; In tetrahydrofuran; mineral oil; at 0 - 45 ℃; Inert atmosphere;
DOI:10.1007/s11426-010-4065-1

Reference yield:

: 182197-78-0
(S)-1-benzyloxycarbonyl-3-(tert-butyldimethylsilyloxy)-2-pyrrolidinone

: 1257424-01-3
(1S,8R,8aR)-8-benzyloxy-1-(tert-butyldimethylsilyloxy)-5-indolizidinone

Guidance literature:: Multi-step reaction with 5 steps

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

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

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

4.1: 10% palladium on activated carbon; hydrogen; triethylamine / methanol / 20 °C

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

5.2: 0 - 45 °C / Inert atmosphere

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

Reference yield:

: (1S,8R/S,8aR)-1-(tert-butyldimethylsilyloxy)-8-hydroxy-5-indolizidinone

: 1257424-01-3
(1S,8R,8aR)-8-benzyloxy-1-(tert-butyldimethylsilyloxy)-5-indolizidinone

Guidance literature:: Multi-step reaction with 3 steps

1.1: dipyridinium dichromate / dichloromethane / 8 h / 20 °C / Molecular sieve

2.1: sodium tetrahydroborate / methanol / 0.75 h / -60 - -55 °C

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

3.2: 0 - 45 °C / Inert atmosphere

With sodium tetrahydroborate; dipyridinium dichromate; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; mineral oil;
DOI:10.1007/s11426-010-4065-1