(3S,6R,8R,8aR)-8-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-hydroxy-hexahydro-indolizin-5-one

Base Information

Chemical Name:(3S,6R,8R,8aR)-8-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-hydroxy-hexahydro-indolizin-5-one
CAS No.:181705-75-9
Molecular Formula:C₃₂H₃₉NO₄Si
Molecular Weight:529.751
Hs Code.:

Synonyms:(3S,6R,8R,8aR)-8-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-hydroxy-hexahydro-indolizin-5-one

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Chemical Property of (3S,6R,8R,8aR)-8-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-hydroxy-hexahydro-indolizin-5-one

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Technology Process of (3S,6R,8R,8aR)-8-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-hydroxy-hexahydro-indolizin-5-one

There total 9 articles about (3S,6R,8R,8aR)-8-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-hydroxy-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: 81.0%

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

: 181705-75-9
(3S,6R,8R,8aR)-8-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-hydroxy-hexahydro-indolizin-5-one

Guidance literature:: With tert.-butyl lithium; oxygen; ammonium chloride; phosphorous acid trimethyl ester; In tetrahydrofuran; at -78 ℃; for 0.3h;
DOI:10.1016/S0960-894X(96)00275-2

Reference yield:

: 100-39-0
benzyl bromide

: 181705-75-9
(3S,6R,8R,8aR)-8-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-hydroxy-hexahydro-indolizin-5-one

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / NaH, TBAI / tetrahydrofuran / 18 h

2: 81 percent / t-BuLi, O₂, (MeO)3P, NH₄Cl / tetrahydrofuran / 0.3 h / -78 °C

With tert.-butyl lithium; oxygen; tetra-(n-butyl)ammonium iodide; sodium hydride; ammonium chloride; phosphorous acid trimethyl ester; In tetrahydrofuran;
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

: 181705-75-9
(3S,6R,8R,8aR)-8-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-hydroxy-hexahydro-indolizin-5-one

Guidance literature:: Multi-step reaction with 7 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

7: 81 percent / t-BuLi, O₂, (MeO)3P, NH₄Cl / tetrahydrofuran / 0.3 h / -78 °C

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