(3S,8R,8aR)-8-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-hexahydro-indolizin-5-one

Base Information

Chemical Name:(3S,8R,8aR)-8-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-hexahydro-indolizin-5-one
CAS No.:181705-74-8
Molecular Formula:C₃₂H₃₉NO₃Si
Molecular Weight:513.752
Hs Code.:

Synonyms:(3S,8R,8aR)-8-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-hexahydro-indolizin-5-one

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Chemical Property of (3S,8R,8aR)-8-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-hexahydro-indolizin-5-one

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Technology Process of (3S,8R,8aR)-8-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-hexahydro-indolizin-5-one

There total 7 articles about (3S,8R,8aR)-8-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-hexahydro-indolizin-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: 100.0%

: 100-39-0
benzyl bromide

: 181961-50-2
(3S,8R,8aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-8-hydroxy-hexahydro-indolizin-5-one

: 181705-74-8
(3S,8R,8aR)-8-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-hexahydro-indolizin-5-one

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; for 18h;
DOI:10.1016/S0960-894X(96)00275-2

Reference yield:

: (S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(5-oxo-tetrahydro-furan-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

: 181705-74-8
(3S,8R,8aR)-8-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-hexahydro-indolizin-5-one

Guidance literature:: Multi-step reaction with 6 steps

1: B-bromocatechol borane, NaHCO₃ / CH₂Cl₂ / 0 °C

2: 99 percent / NaOMe / methanol / 1 h / 0 °C

3: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

4: 44 percent / DBU / benzene / 0.5 h / 70 °C

5: LiBEt₃H, NaHCO₃, H₂O₂ / tetrahydrofuran; H₂O / 3 h / -78 - -50 °C

6: 100 percent / NaH, TBAI / tetrahydrofuran / 18 h

With bromocatecholborane; dihydrogen peroxide; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; lithium triethylborohydride; sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; water; benzene;
DOI:10.1016/S0960-894X(96)00275-2

Reference yield:

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

: 181705-74-8
(3S,8R,8aR)-8-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-hexahydro-indolizin-5-one

Guidance literature:: Multi-step reaction with 4 steps

1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

2: 44 percent / DBU / benzene / 0.5 h / 70 °C

3: LiBEt₃H, NaHCO₃, H₂O₂ / tetrahydrofuran; H₂O / 3 h / -78 - -50 °C

4: 100 percent / NaH, TBAI / tetrahydrofuran / 18 h

With dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; lithium triethylborohydride; sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; water; benzene;
DOI:10.1016/S0960-894X(96)00275-2