Trifluoro-methanesulfonic acid (3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enyl ester

Base Information

• Chemical Name: Trifluoro-methanesulfonic acid (3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enyl ester
• CAS No.: 350817-09-3
• Molecular Formula: C₁₃H₂₃F₃O₅SSi
• Molecular Weight: 376.469

Synonyms:Trifluoro-methanesulfonic acid (3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enyl ester

Chemical Property of Trifluoro-methanesulfonic acid (3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enyl ester

Chemical Property:

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Technology Process of Trifluoro-methanesulfonic acid (3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enyl ester

There total 9 articles about Trifluoro-methanesulfonic acid (3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enyl ester 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: 88.0%

Trifluoro-methanesulfonic acid (1S,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-2-en-2-yl ester (350817-05-9) → Trifluoro-methanesulfonic acid (3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enyl ester (350817-09-3)

Guidance literature:

With diborane; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1016/S0040-4039(01)00481-6

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → Trifluoro-methanesulfonic acid (3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enyl ester (350817-09-3)

Guidance literature:

Multi-step reaction with 9 steps

1: imidazole / dimethylformamide / 2 h / 25 °C

2: (iBu)2AlCl; LDA / benzene / 12 h / 25 °C

3: Et₃N; DMAP / CH₂Cl₂ / 5 h / 0 - 20 °C

4: 81 percent / Et₃N; Pd(PPh₃)4 / dioxane / 6 h / Heating

5: oxone; CH₃COCF₃; EDTA / NaHCO₃ / acetonitrile; tetrahydrofuran / 6 h / 0 °C

6: HIO₄; NaIO₄ / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 3 h / 25 °C

7: 85 percent / tBuOOH; Triton B / benzene / 2 h / 5 °C

8: 86 percent / LDA / tetrahydrofuran / 8 h / -78 - 25 °C

9: 88 percent / B₂H₆ / tetrahydrofuran / 2 h / 0 °C

With 1H-imidazole; tert.-butylhydroperoxide; dmap; Oxone; sodium periodate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ethylenediaminetetraacetic acid; 1,1,1-trifluoro-2-propanone; diisobutylaluminum chloride; N-benzyl-trimethylammonium hydroxide; periodic acid; triethylamine; diborane; lithium diisopropyl amide; sodium hydrogencarbonate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4039(01)00481-6

Reference yield:

tert-butyl-dimethyl-(4-methylene-cyclohex-2-enyloxy)-silane (350817-02-6) → Trifluoro-methanesulfonic acid (3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enyl ester (350817-09-3)

Guidance literature:

Multi-step reaction with 5 steps

1: oxone; CH₃COCF₃; EDTA / NaHCO₃ / acetonitrile; tetrahydrofuran / 6 h / 0 °C

2: HIO₄; NaIO₄ / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 3 h / 25 °C

3: 85 percent / tBuOOH; Triton B / benzene / 2 h / 5 °C

4: 86 percent / LDA / tetrahydrofuran / 8 h / -78 - 25 °C

5: 88 percent / B₂H₆ / tetrahydrofuran / 2 h / 0 °C

With tert.-butylhydroperoxide; Oxone; sodium periodate; ethylenediaminetetraacetic acid; 1,1,1-trifluoro-2-propanone; N-benzyl-trimethylammonium hydroxide; periodic acid; diborane; lithium diisopropyl amide; sodium hydrogencarbonate; In tetrahydrofuran; water; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4039(01)00481-6

upstream raw materials:

Trifluoro-methanesulfonic acid (1S,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-2-en-2-yl ester

tert-butyldimethylsilyl chloride

<(4R)-(+)-tert-Butoxydimethylsiloxy>-2-cyclohexen-1-on

tert-butyl-dimethyl-(4-methylene-cyclohex-2-enyloxy)-silane

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