(1S,2S,10bS)-1,2,3,10b-tetrahydro-1-ethoxycarbonylmethyl-10b-phenylsulfanyl-2-(tert-butyldiphenylsilyl)oxypyrido[2,1-a]isoindol-6(4H)-one

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Chemical Name:(1S,2S,10bS)-1,2,3,10b-tetrahydro-1-ethoxycarbonylmethyl-10b-phenylsulfanyl-2-(tert-butyldiphenylsilyl)oxypyrido[2,1-a]isoindol-6(4H)-one
CAS No.:287728-26-1
Molecular Formula:C₃₈H₄₁NO₄SSi
Molecular Weight:635.899
Hs Code.:

Synonyms:(1S,2S,10bS)-1,2,3,10b-tetrahydro-1-ethoxycarbonylmethyl-10b-phenylsulfanyl-2-(tert-butyldiphenylsilyl)oxypyrido[2,1-a]isoindol-6(4H)-one

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Chemical Property of (1S,2S,10bS)-1,2,3,10b-tetrahydro-1-ethoxycarbonylmethyl-10b-phenylsulfanyl-2-(tert-butyldiphenylsilyl)oxypyrido[2,1-a]isoindol-6(4H)-one

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Technology Process of (1S,2S,10bS)-1,2,3,10b-tetrahydro-1-ethoxycarbonylmethyl-10b-phenylsulfanyl-2-(tert-butyldiphenylsilyl)oxypyrido[2,1-a]isoindol-6(4H)-one

There total 9 articles about (1S,2S,10bS)-1,2,3,10b-tetrahydro-1-ethoxycarbonylmethyl-10b-phenylsulfanyl-2-(tert-butyldiphenylsilyl)oxypyrido[2,1-a]isoindol-6(4H)-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: 77.0%

: 287728-22-7
ethyl (2E,4S)-6-(1,3-dihydro-3-phenylsulfanyl-1-oxoisoindol-2-yl)-4-(tert-butyldiphenylsilyl)oxyhex-2-enoate

: 287728-26-1
(1S,2S,10bS)-1,2,3,10b-tetrahydro-1-ethoxycarbonylmethyl-10b-phenylsulfanyl-2-(tert-butyldiphenylsilyl)oxypyrido[2,1-a]isoindol-6(4H)-one

: (1R,2S,10bR)-1,2,3,10b-tetrahydro-1-ethoxycarbonylmethyl-10b-phenylsulfanyl-2-(tert-butyldiphenylsilyl)oxypyrido[2,1-a]isoindol-6(4H)-one

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/S0040-4039(00)00485-8

Reference yield:

: 287728-31-8
(S)-4-phthalimido-1,2-butanediol

: 287728-26-1
(1S,2S,10bS)-1,2,3,10b-tetrahydro-1-ethoxycarbonylmethyl-10b-phenylsulfanyl-2-(tert-butyldiphenylsilyl)oxypyrido[2,1-a]isoindol-6(4H)-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 97 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

2.1: imidazole / CH₂Cl₂; dimethylformamide / 20 °C

2.2: 89 percent / aq. HF / acetonitrile / 20 °C

3.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 0 °C

4.1: 5.78 g / CH₂Cl₂ / 20 °C

5.1: 92 percent / NaBH₄ / methanol; tetrahydrofuran / -20 °C

6.1: 97 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / -78 °C

7.1: 77 percent / LDA / tetrahydrofuran; hexane / 1 h / -78 °C

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; boron trifluoride diethyl etherate; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 3.1: Swern oxidation;
DOI:10.1039/b303031h

Reference yield:

: 618388-42-4
(S)-4-phthalimido-2-(tert-butyldiphenylsilyl)oxy-1-butanal

: 287728-26-1
(1S,2S,10bS)-1,2,3,10b-tetrahydro-1-ethoxycarbonylmethyl-10b-phenylsulfanyl-2-(tert-butyldiphenylsilyl)oxypyrido[2,1-a]isoindol-6(4H)-one

Guidance literature:: Multi-step reaction with 4 steps

1: 5.78 g / CH₂Cl₂ / 20 °C

2: 92 percent / NaBH₄ / methanol; tetrahydrofuran / -20 °C

3: 97 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / -78 °C

4: 77 percent / LDA / tetrahydrofuran; hexane / 1 h / -78 °C

With sodium tetrahydroborate; boron trifluoride diethyl etherate; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1039/b303031h