<2S-(1E,2α,3β,5α)>-<3,5-bis<<(1,1dimethylethyl)dimethylsilyl>oxy>-2-hydroxy-2-methylcyclohexylidene>acetic acid ethyl ester

Base Information

Chemical Name:<2S-(1E,2α,3β,5α)>-<3,5-bis<<(1,1dimethylethyl)dimethylsilyl>oxy>-2-hydroxy-2-methylcyclohexylidene>acetic acid ethyl ester
CAS No.:81506-22-1
Molecular Formula:C₂₃H₄₆O₅Si₂
Molecular Weight:458.786
Hs Code.:

Synonyms:<2S-(1E,2α,3β,5α)>-<3,5-bis<<(1,1dimethylethyl)dimethylsilyl>oxy>-2-hydroxy-2-methylcyclohexylidene>acetic acid ethyl ester

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Chemical Property of <2S-(1E,2α,3β,5α)>-<3,5-bis<<(1,1dimethylethyl)dimethylsilyl>oxy>-2-hydroxy-2-methylcyclohexylidene>acetic acid ethyl ester

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Technology Process of <2S-(1E,2α,3β,5α)>-<3,5-bis<<(1,1dimethylethyl)dimethylsilyl>oxy>-2-hydroxy-2-methylcyclohexylidene>acetic acid ethyl ester

There total 8 articles about <2S-(1E,2α,3β,5α)>-<3,5-bis<<(1,1dimethylethyl)dimethylsilyl>oxy>-2-hydroxy-2-methylcyclohexylidene>acetic acid ethyl 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: 95.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 81506-21-0
<2S-(1E,2α,3β,5α)>-(2,3,5-trihydroxy-2-methylcyclohexylidene)acetic acid ethyl ester

: 81506-22-1
<2S-(1E,2α,3β,5α)>-<3,5-bis<<(1,1dimethylethyl)dimethylsilyl>oxy>-2-hydroxy-2-methylcyclohexylidene>acetic acid ethyl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 25 ℃;
DOI:10.1021/ja00374a052

Reference yield:

: 81506-17-4
<2S-(1E,2α,3β,5α)>-<2-(acetyloxy)-3-hydroxy-2-methyl-5-(1-methylethenyl)cyclohexylidene>acetic acid ethyl ester

: 81506-22-1
<2S-(1E,2α,3β,5α)>-<3,5-bis<<(1,1dimethylethyl)dimethylsilyl>oxy>-2-hydroxy-2-methylcyclohexylidene>acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / Ac₂O, pyridine / 15 h / Ambient temperature

2: 97 percent / aq.OsO₄, KIO₄ / tetrahydrofuran; H₂O / 16 h / Ambient temperature

3: 85 percent / 90percent H₂O₂, trifluoroacetic anhydride, KH₂PO₄ / CH₂Cl₂ / 0 °C

4: cation exchange resin AG 50W-X₄ / ethanol / 50 °C

5: NaOEt / ethanol / 2 h / Ambient temperature

6: 95 percent / imidazole / dimethylformamide / Ambient temperature

With pyridine; 1H-imidazole; potassium dihydrogenphosphate; osmium(VIII) oxide; potassium metaperiodate; cation exchange resin AG 50W-X₄; dihydrogen peroxide; sodium ethanolate; acetic anhydride; trifluoroacetic anhydride; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo00366a004

Reference yield:

: 39903-97-4
(S)-carvone oxide

: 81506-22-1
<2S-(1E,2α,3β,5α)>-<3,5-bis<<(1,1dimethylethyl)dimethylsilyl>oxy>-2-hydroxy-2-methylcyclohexylidene>acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) NaH / 1.) THF, RT, 1.5 h, 2.) THF, 20 h

2: 84 percent / NaOAc, AcOH / 16 h / 50 °C

3: 92 percent / Ac₂O, pyridine / 15 h / Ambient temperature

4: 97 percent / aq.OsO₄, KIO₄ / tetrahydrofuran; H₂O / 16 h / Ambient temperature

5: 85 percent / 90percent H₂O₂, trifluoroacetic anhydride, KH₂PO₄ / CH₂Cl₂ / 0 °C

6: cation exchange resin AG 50W-X₄ / ethanol / 50 °C

7: NaOEt / ethanol / 2 h / Ambient temperature

8: 95 percent / imidazole / dimethylformamide / Ambient temperature

With pyridine; 1H-imidazole; potassium dihydrogenphosphate; osmium(VIII) oxide; potassium metaperiodate; cation exchange resin AG 50W-X₄; dihydrogen peroxide; sodium ethanolate; sodium acetate; acetic anhydride; sodium hydride; acetic acid; trifluoroacetic anhydride; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo00366a004