(1S,4R,6S)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-ol

Base Information

Chemical Name:(1S,4R,6S)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-ol
CAS No.:1268868-62-7
Molecular Formula:C₂₇H₃₈O₅Si
Molecular Weight:470.681
Hs Code.:

Synonyms:(1S,4R,6S)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-ol

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Chemical Property of (1S,4R,6S)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-ol

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Technology Process of (1S,4R,6S)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-ol

There total 2 articles about (1S,4R,6S)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-ol 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:

: 1268868-61-6
(4R,6S)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-one

: 1268868-62-7
(1S,4R,6S)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-ol

: (1R,4R,6S)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-ol

Guidance literature:: (4R,6S)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-one; With cerium(III) chloride heptahydrate; In methanol; dichloromethane; at 20 ℃; for 1h;

With sodium tetrahydroborate; In methanol; dichloromethane; at -78 ℃; for 0.5h;
DOI:10.3987/COM-10-S(E)27

Reference yield:

: C₂₇H₃₈O₅Si

: 1268868-62-7
(1S,4R,6S)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-ol

: (1R,4R,6S)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: N,N,N,N,-tetramethylethylenediamine / dichloromethane / 1 h / 60 °C / Molecular sieve

1.2: Silica gel / 1 h / 20 °C

2.1: cerium(III) chloride heptahydrate / dichloromethane; methanol / 1 h / 20 °C

2.2: 0.5 h / -78 °C

With N,N,N,N,-tetramethylethylenediamine; cerium(III) chloride heptahydrate; In methanol; dichloromethane;
DOI:10.3987/COM-10-S(E)27

Reference yield:

: 1268868-62-7
(1S,4R,6S)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-ol

: 357-70-0
Galantamine

Guidance literature:: Multi-step reaction with 7 steps

1.1: 2-hydroxynitrobenzene / 52 h / 140 °C / Sealed tube; Inert atmosphere

2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 12 h / 0 °C

3.1: palladium 10% on activated carbon; hydrogen / ethanol / 1 h / 20 °C

3.2: 1 h / 20 °C

4.1: dmap; 1,1'-Thiocarbonyldiimidazole / 1,2-dichloro-benzene / 6 h / Reflux

5.1: lithium hydroxide monohydrate / ethanol; water / 20 h / 20 °C

6.1: trifluoroacetic acid / 1,2-dichloro-ethane / 2.5 h / 20 °C

7.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Inert atmosphere; Reflux

With dmap; N-Bromosuccinimide; lithium aluminium tetrahydride; lithium hydroxide monohydrate; palladium 10% on activated carbon; hydrogen; 1,1'-Thiocarbonyldiimidazole; trifluoroacetic acid; 2-hydroxynitrobenzene; In tetrahydrofuran; ethanol; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1,2-dichloro-benzene; 6.1: |Pictet-Spengler Synthesis;
DOI:10.3987/COM-10-S(E)27