(S)-1-(t-butyldimethylsiloxy)-2-{3'-[N-(carbomethoxy)-N-(phenylselanylmethyl)amino]}-propyl-3-phenylsulfonyl-2-cyclohexene

Base Information

Chemical Name:(S)-1-(t-butyldimethylsiloxy)-2-{3'-[N-(carbomethoxy)-N-(phenylselanylmethyl)amino]}-propyl-3-phenylsulfonyl-2-cyclohexene
CAS No.:470458-67-4
Molecular Formula:C₃₀H₄₃NO₅SSeSi
Molecular Weight:636.787
Hs Code.:

Synonyms:(S)-1-(t-butyldimethylsiloxy)-2-{3'-[N-(carbomethoxy)-N-(phenylselanylmethyl)amino]}-propyl-3-phenylsulfonyl-2-cyclohexene

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Chemical Property of (S)-1-(t-butyldimethylsiloxy)-2-{3'-[N-(carbomethoxy)-N-(phenylselanylmethyl)amino]}-propyl-3-phenylsulfonyl-2-cyclohexene

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Technology Process of (S)-1-(t-butyldimethylsiloxy)-2-{3'-[N-(carbomethoxy)-N-(phenylselanylmethyl)amino]}-propyl-3-phenylsulfonyl-2-cyclohexene

There total 12 articles about (S)-1-(t-butyldimethylsiloxy)-2-{3'-[N-(carbomethoxy)-N-(phenylselanylmethyl)amino]}-propyl-3-phenylsulfonyl-2-cyclohexene 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: 71.0%

: 645-96-5
Benzeneselenol

: 470458-78-7
1-(t-butyldimethylsiloxy)-2-{3'-[N-(carbomethoxy)-N-(hydroxymethyl)amino]}propyl-3-phenylsulfonyl-2-cyclohexene

: 470458-67-4
(S)-1-(t-butyldimethylsiloxy)-2-{3'-[N-(carbomethoxy)-N-(phenylselanylmethyl)amino]}-propyl-3-phenylsulfonyl-2-cyclohexene

Guidance literature:: With toluene-4-sulfonic acid; at 20 ℃; for 2h;
DOI:10.1021/ol026671e

Reference yield:

: 75717-39-4
3-(phenylsulfanyl)cyclohex-2-en-1-one

: 470458-67-4
(S)-1-(t-butyldimethylsiloxy)-2-{3'-[N-(carbomethoxy)-N-(phenylselanylmethyl)amino]}-propyl-3-phenylsulfonyl-2-cyclohexene

Guidance literature:: Multi-step reaction with 9 steps

1: 81 percent / N-bromosuccinimide / CCl₄ / 24 h / 20 °C

2: 96 percent / cerium chloride heptahydrate; sodium borohydride / methanol / 0.5 h / 20 °C

3: 77 percent / DMAP; DCC / CH₂Cl₂ / 4 h / 20 °C

4: 97 percent / LiBH₄ / tetrahydrofuran / 12 h / 20 °C

5: 95 percent / imidazole / dimethylformamide / 12 h / 20 °C

6: 83 percent / NaOH / Pd(PPh₃)4 / tetrahydrofuran; H₂O / 3 h / Heating

7: 98 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 2.5 h / 20 °C

8: 75 percent / t-BuOK / 2-methyl-propan-2-ol / 1 h / 20 °C

9: 71 percent / p-toluenesulfonic acid / 2 h / 20 °C

With 1H-imidazole; dmap; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; lithium borohydride; cerium(III) chloride; potassium tert-butylate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 6: Suzuki coupling reaction;
DOI:10.1021/ol026671e

Reference yield:

: 470458-71-0
2-bromo-3-(phenylsulfanyl)cyclohex-2-en-1-one

: 470458-67-4
(S)-1-(t-butyldimethylsiloxy)-2-{3'-[N-(carbomethoxy)-N-(phenylselanylmethyl)amino]}-propyl-3-phenylsulfonyl-2-cyclohexene

Guidance literature:: Multi-step reaction with 8 steps

1: 96 percent / cerium chloride heptahydrate; sodium borohydride / methanol / 0.5 h / 20 °C

2: 77 percent / DMAP; DCC / CH₂Cl₂ / 4 h / 20 °C

3: 97 percent / LiBH₄ / tetrahydrofuran / 12 h / 20 °C

4: 95 percent / imidazole / dimethylformamide / 12 h / 20 °C

5: 83 percent / NaOH / Pd(PPh₃)4 / tetrahydrofuran; H₂O / 3 h / Heating

6: 98 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 2.5 h / 20 °C

7: 75 percent / t-BuOK / 2-methyl-propan-2-ol / 1 h / 20 °C

8: 71 percent / p-toluenesulfonic acid / 2 h / 20 °C

With 1H-imidazole; dmap; sodium hydroxide; sodium tetrahydroborate; lithium borohydride; cerium(III) chloride; potassium tert-butylate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 5: Suzuki coupling reaction;
DOI:10.1021/ol026671e