5(S)-(2-hydroxy-1-oxoethyl)-5-<(trimethylsilyl)oxy>-6(S)-<((tert-butyldimethylsilyl)oxy)methyl>-2-methyl-1,3-cyclohexadiene

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Chemical Name:5(S)-(2-hydroxy-1-oxoethyl)-5-<(trimethylsilyl)oxy>-6(S)-<((tert-butyldimethylsilyl)oxy)methyl>-2-methyl-1,3-cyclohexadiene
CAS No.:114179-39-4
Molecular Formula:C₁₉H₃₆O₄Si₂
Molecular Weight:384.663
Hs Code.:

Synonyms:5(S)-(2-hydroxy-1-oxoethyl)-5-<(trimethylsilyl)oxy>-6(S)-<((tert-butyldimethylsilyl)oxy)methyl>-2-methyl-1,3-cyclohexadiene

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Chemical Property of 5(S)-(2-hydroxy-1-oxoethyl)-5-<(trimethylsilyl)oxy>-6(S)-<((tert-butyldimethylsilyl)oxy)methyl>-2-methyl-1,3-cyclohexadiene

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Technology Process of 5(S)-(2-hydroxy-1-oxoethyl)-5-<(trimethylsilyl)oxy>-6(S)-<((tert-butyldimethylsilyl)oxy)methyl>-2-methyl-1,3-cyclohexadiene

There total 19 articles about 5(S)-(2-hydroxy-1-oxoethyl)-5-<(trimethylsilyl)oxy>-6(S)-<((tert-butyldimethylsilyl)oxy)methyl>-2-methyl-1,3-cyclohexadiene 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:

: 179917-78-3
(5S,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-5-trimethylsilanyloxy-5-(1-trimethylsilanyloxy-vinyl)-cyclohexa-1,3-diene

: 114179-39-4
5(S)-(2-hydroxy-1-oxoethyl)-5-<(trimethylsilyl)oxy>-6(S)-<((tert-butyldimethylsilyl)oxy)methyl>-2-methyl-1,3-cyclohexadiene

Guidance literature:: With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 0.5h; Yield given;
DOI:10.1021/ja961071u

Reference yield:

: 13369-24-9
(E)-ethyl 4-methylpenta-2,4-dienoate

: 114179-39-4
5(S)-(2-hydroxy-1-oxoethyl)-5-<(trimethylsilyl)oxy>-6(S)-<((tert-butyldimethylsilyl)oxy)methyl>-2-methyl-1,3-cyclohexadiene

Guidance literature:: Multi-step reaction with 10 steps

1: LiAlH₄ / diethyl ether

2: 100 percent / 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / Ambient temperature

3: 98 percent / hydroquinone / benzene / 24 h / 110 - 120 °C

4: 98 percent / LiAlH₄ / diethyl ether / 0.08 h / -78 °C

5: 100 percent / titanium isopropoxide, (+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂ / -20 °C

6: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, from -60 deg C to RT

7: tetrahydrofuran; diethyl ether / 3 h

8: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min

9: 1.) LDA / 1.) THF, -78 deg C, 35 min, 2.) THF, -78 deg C, 15 min

10: m-CPBA, NaHCO₃ / CH₂Cl₂ / 0.5 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; oxalyl dichloride; sodium hydrogencarbonate; dimethyl sulfoxide; (+)-Weinsaeure-diethylester; triethylamine; hydroquinone; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1021/ja961071u

Reference yield:

: 67065-89-8
(2E)-4-methylpenta-2,4-dien-1-ol

: 114179-39-4
5(S)-(2-hydroxy-1-oxoethyl)-5-<(trimethylsilyl)oxy>-6(S)-<((tert-butyldimethylsilyl)oxy)methyl>-2-methyl-1,3-cyclohexadiene

Guidance literature:: Multi-step reaction with 9 steps

1: 100 percent / 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / Ambient temperature

2: 98 percent / hydroquinone / benzene / 24 h / 110 - 120 °C

3: 98 percent / LiAlH₄ / diethyl ether / 0.08 h / -78 °C

4: 100 percent / titanium isopropoxide, (+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂ / -20 °C

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, from -60 deg C to RT

6: tetrahydrofuran; diethyl ether / 3 h

7: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min

8: 1.) LDA / 1.) THF, -78 deg C, 35 min, 2.) THF, -78 deg C, 15 min

9: m-CPBA, NaHCO₃ / CH₂Cl₂ / 0.5 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; oxalyl dichloride; sodium hydrogencarbonate; dimethyl sulfoxide; (+)-Weinsaeure-diethylester; triethylamine; hydroquinone; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1021/ja961071u