(3S,8S,9R)-3-(tert-butyldiphenylsilanyloxymethyl)-8-hydroxyhexahydroindolizin-5-one

Base Information

Chemical Name:(3S,8S,9R)-3-(tert-butyldiphenylsilanyloxymethyl)-8-hydroxyhexahydroindolizin-5-one
CAS No.:181705-72-6
Molecular Formula:C₂₅H₃₃NO₃Si
Molecular Weight:423.627
Hs Code.:

Synonyms:(3S,8S,9R)-3-(tert-butyldiphenylsilanyloxymethyl)-8-hydroxyhexahydroindolizin-5-one

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Chemical Property of (3S,8S,9R)-3-(tert-butyldiphenylsilanyloxymethyl)-8-hydroxyhexahydroindolizin-5-one

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Technology Process of (3S,8S,9R)-3-(tert-butyldiphenylsilanyloxymethyl)-8-hydroxyhexahydroindolizin-5-one

There total 38 articles about (3S,8S,9R)-3-(tert-butyldiphenylsilanyloxymethyl)-8-hydroxyhexahydroindolizin-5-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: 99.0%

: 181705-71-5
(5S,2'S,5'S)-5-[5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'yl]-tetrahydrofuran-2-one

: 181705-72-6
(3S,8S,9R)-3-(tert-butyldiphenylsilanyloxymethyl)-8-hydroxyhexahydroindolizin-5-one

Guidance literature:: With sodium methylate; In methanol; at 0 ℃; for 1h;
DOI:10.1016/S0960-894X(96)00275-2

Reference yield:

: 138629-30-8,138871-56-4
(S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate

: 181705-72-6
(3S,8S,9R)-3-(tert-butyldiphenylsilanyloxymethyl)-8-hydroxyhexahydroindolizin-5-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: diisobutylaluminium hydride / toluene / 1.5 h / -78 °C

2.1: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / 20 °C

3.1: CuBr*Me₂S / diethyl ether; tetrahydrofuran / 0.67 h / -40 °C

3.2: 1.1 g / boron trifluoride diethyl etherate / diethyl ether; tetrahydrofuran / 5 h / -40 - 0 °C

4.1: TMSOTf; i-Pr₂NEt / CH₂Cl₂ / 1.5 h / 0 °C

5.1: EDC; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.75 h

6.1: 2.14 g / Cl₂(Cy₃P)2Ru=CHPh / CH₂Cl₂ / 15 h / Heating

7.1: 78 percent / urea-hydrogen peroxide; trifluoroacetic acid / CH₂Cl₂ / 2 h / 0 °C

8.1: 92 percent / LDA / tetrahydrofuran; hexane / 0.42 h / -78 °C

9.1: 99 percent / hydrogen / Pd/C / ethyl acetate / 6 h / 20 °C

With dmap; Grubbs catalyst first generation; copper(I) bromide dimethylsulfide complex; trimethylsilyl trifluoromethanesulfonate; urea-hydrogen peroxide; hydrogen; diisobutylaluminium hydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; toluene; 6.1: Grubbs ring-closure metathesis reaction;

Reference yield:

: 192389-43-8
(5S)-1-(benzyloxycarbonyl)-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-hydroxypyrrolidine

: 181705-72-6
(3S,8S,9R)-3-(tert-butyldiphenylsilanyloxymethyl)-8-hydroxyhexahydroindolizin-5-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / 20 °C

2.1: CuBr*Me₂S / diethyl ether; tetrahydrofuran / 0.67 h / -40 °C

2.2: 1.1 g / boron trifluoride diethyl etherate / diethyl ether; tetrahydrofuran / 5 h / -40 - 0 °C

3.1: TMSOTf; i-Pr₂NEt / CH₂Cl₂ / 1.5 h / 0 °C

4.1: EDC; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.75 h

5.1: 2.14 g / Cl₂(Cy₃P)2Ru=CHPh / CH₂Cl₂ / 15 h / Heating

6.1: 78 percent / urea-hydrogen peroxide; trifluoroacetic acid / CH₂Cl₂ / 2 h / 0 °C

7.1: 92 percent / LDA / tetrahydrofuran; hexane / 0.42 h / -78 °C

8.1: 99 percent / hydrogen / Pd/C / ethyl acetate / 6 h / 20 °C

With dmap; Grubbs catalyst first generation; copper(I) bromide dimethylsulfide complex; trimethylsilyl trifluoromethanesulfonate; urea-hydrogen peroxide; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; 5.1: Grubbs ring-closure metathesis reaction;