(1S,1'R,2S,3S)-3-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-6-methylenecyclohexane-1,2-diol

Base Information

Chemical Name:(1S,1'R,2S,3S)-3-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-6-methylenecyclohexane-1,2-diol
CAS No.:252289-46-6
Molecular Formula:C₁₈H₃₆O₃Si
Molecular Weight:328.568
Hs Code.:

Synonyms:(1S,1'R,2S,3S)-3-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-6-methylenecyclohexane-1,2-diol

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Chemical Property of (1S,1'R,2S,3S)-3-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-6-methylenecyclohexane-1,2-diol

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Technology Process of (1S,1'R,2S,3S)-3-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-6-methylenecyclohexane-1,2-diol

There total 10 articles about (1S,1'R,2S,3S)-3-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-6-methylenecyclohexane-1,2-diol 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: 90.0%

: (4S,5S)-4-{(R)-2-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-1-methyl-ethyl}-1-methyl-5-trimethylsilanyloxy-7-oxa-bicyclo[4.1.0]heptane

: (1R,2S,3S)-3-{(R)-2-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-1-methyl-ethyl}-6-methylene-cyclohexane-1,2-diol

: 252289-46-6
(1S,1'R,2S,3S)-3-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-6-methylenecyclohexane-1,2-diol

Guidance literature:: With lithium diethylamide; In tetrahydrofuran; for 2h; Heating;
DOI:10.1002/(SICI)1522-2675(19991006)82:10<1610::AID-HLCA1610>3.0.CO;2-T

Reference yield:

: 13834-07-6
(1R,3R,4S,8R)-9-hydroxy-p-menthol

: 252289-46-6
(1S,1'R,2S,3S)-3-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-6-methylenecyclohexane-1,2-diol

Guidance literature:: Multi-step reaction with 9 steps

1: 91 percent / 1H-imidazole / dimethylformamide / 15 h / 0 - 20 °C

2: 62 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3 h / -79 °C

3: 100 percent / BuLi; (i-Pr)2NH / hexane; tetrahydrofuran / 1 h / -78 °C

4: N-bromosuccinimide / tetrahydrofuran / 2 h / 0 °C

5: 74 percent / 2,4,6-trimethyl-pyridine / 1 h / 145 - 150 °C

6: 96 percent / H₂O₂; NaOH / methanol / 0 °C

7: 95 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 1 h / 0 - 20 °C

8: 100 percent / Et₃N / tetrahydrofuran / 14 h / 0 - 20 °C

9: 90 percent / LiNEt₂ / tetrahydrofuran / 2 h / Heating

With 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; cerium(III) chloride; oxalyl dichloride; lithium diethylamide; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; diisopropylamine; In tetrahydrofuran; 2,4,6-trimethyl-pyridine; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Oxidation / 3: Etherification / 4: Bromination / 5: Dehydrobromination / 6: Epoxidation / 7: Reduction / 8: Substitution / 9: Rearrangement;
DOI:10.1002/(SICI)1522-2675(19991006)82:10<1610::AID-HLCA1610>3.0.CO;2-T

Reference yield:

: 7786-67-6,18674-65-2,20549-46-6,21290-09-5,29141-10-4,50373-36-9,59905-53-2,59905-54-3,96612-21-4,104870-56-6,121468-66-4,122517-60-6,122517-61-7,144541-38-8,89-79-2
isopulegol

: 252289-46-6
(1S,1'R,2S,3S)-3-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-6-methylenecyclohexane-1,2-diol

Guidance literature:: Multi-step reaction with 10 steps

1.1: B₂H₆ / tetrahydrofuran / 2 h / 0 - 20 °C

1.2: NaOH; H₂O₂ / 0.5 h / Heating

2.1: 91 percent / 1H-imidazole / dimethylformamide / 15 h / 0 - 20 °C

3.1: 62 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3 h / -79 °C

4.1: 100 percent / BuLi; (i-Pr)2NH / hexane; tetrahydrofuran / 1 h / -78 °C

5.1: N-bromosuccinimide / tetrahydrofuran / 2 h / 0 °C

6.1: 74 percent / 2,4,6-trimethyl-pyridine / 1 h / 145 - 150 °C

7.1: 96 percent / H₂O₂; NaOH / methanol / 0 °C

8.1: 95 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 1 h / 0 - 20 °C

9.1: 100 percent / Et₃N / tetrahydrofuran / 14 h / 0 - 20 °C

10.1: 90 percent / LiNEt₂ / tetrahydrofuran / 2 h / Heating

With 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; cerium(III) chloride; oxalyl dichloride; lithium diethylamide; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; diisopropylamine; diborane; In tetrahydrofuran; 2,4,6-trimethyl-pyridine; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: hydroboration / 1.2: Oxidation / 2.1: Substitution / 3.1: Oxidation / 4.1: Etherification / 5.1: Bromination / 6.1: Dehydrobromination / 7.1: Epoxidation / 8.1: Reduction / 9.1: Substitution / 10.1: Rearrangement;
DOI:10.1002/(SICI)1522-2675(19991006)82:10<1610::AID-HLCA1610>3.0.CO;2-T