5(R)-<<(1',1'-Dimethylethyl)dimethylsilyl>oxy>-3(S)-hydroxy-2,6,6-trimethylcyclohexen-1-carboxaldehyde

Base Information

Chemical Name:5(R)-<<(1',1'-Dimethylethyl)dimethylsilyl>oxy>-3(S)-hydroxy-2,6,6-trimethylcyclohexen-1-carboxaldehyde
CAS No.:171012-26-3
Molecular Formula:C₁₆H₃₀O₃Si
Molecular Weight:298.498
Hs Code.:

Synonyms:5(R)-<<(1',1'-Dimethylethyl)dimethylsilyl>oxy>-3(S)-hydroxy-2,6,6-trimethylcyclohexen-1-carboxaldehyde

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Chemical Property of 5(R)-<<(1',1'-Dimethylethyl)dimethylsilyl>oxy>-3(S)-hydroxy-2,6,6-trimethylcyclohexen-1-carboxaldehyde

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Technology Process of 5(R)-<<(1',1'-Dimethylethyl)dimethylsilyl>oxy>-3(S)-hydroxy-2,6,6-trimethylcyclohexen-1-carboxaldehyde

There total 8 articles about 5(R)-<<(1',1'-Dimethylethyl)dimethylsilyl>oxy>-3(S)-hydroxy-2,6,6-trimethylcyclohexen-1-carboxaldehyde 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: 89.0%

: 171012-25-2
3(R)-<<(1',1'-Dimethylethyl)dimethylsilyl>oxy>-5(R),6(S)-oxido-2,2,6-trimethylcyclohexan-1(R)-carboxaldehyde

: 171012-26-3
5(R)-<<(1',1'-Dimethylethyl)dimethylsilyl>oxy>-3(S)-hydroxy-2,6,6-trimethylcyclohexen-1-carboxaldehyde

Guidance literature:: With sodium methylate; In tetrahydrofuran; at 0 ℃; for 0.25h;
DOI:10.1021/jo00127a028

Reference yield:

: 61302-42-9
(R,E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-ol

: 171012-26-3
5(R)-<<(1',1'-Dimethylethyl)dimethylsilyl>oxy>-3(S)-hydroxy-2,6,6-trimethylcyclohexen-1-carboxaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1: 98 percent / Et₃N / diethyl ether / 3 h / Ambient temperature

2: 50 percent / SnCl₄ / CH₂Cl₂; toluene / 1 h / 0 °C

3: 98 percent / m-CPBA / CH₂Cl₂ / 2 h

4: DBU / benzene

5: 89 percent / (i-Pr)2NH, 4-(dimethylamino)pyridine / dimethylformamide / 24 h / 45 °C

6: 98 percent / K₂CO₃ / methanol / 1 h

7: 86 percent / PCC, NaOAc / CH₂Cl₂ / 3 h / Ambient temperature

8: 89 percent / NaOMe / tetrahydrofuran / 0.25 h / 0 °C

With dmap; sodium methylate; sodium acetate; tin(IV) chloride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/jo00127a028

Reference yield:

: 171012-24-1
3(R)-(Hydroxymethyl)-4(R),5(S)-oxido-2,2,4-trimethylcyclohexan-1(R)-ol

: 171012-26-3
5(R)-<<(1',1'-Dimethylethyl)dimethylsilyl>oxy>-3(S)-hydroxy-2,6,6-trimethylcyclohexen-1-carboxaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1: DBU / benzene

2: 89 percent / (i-Pr)2NH, 4-(dimethylamino)pyridine / dimethylformamide / 24 h / 45 °C

3: 98 percent / K₂CO₃ / methanol / 1 h

4: 86 percent / PCC, NaOAc / CH₂Cl₂ / 3 h / Ambient temperature

5: 89 percent / NaOMe / tetrahydrofuran / 0.25 h / 0 °C

With dmap; sodium methylate; sodium acetate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00127a028