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

Base Information

Chemical Name:(1R,4S,6R)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-ol
CAS No.:951396-65-9
Molecular Formula:C₂₇H₃₈O₅Si
Molecular Weight:470.681
Hs Code.:

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

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

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

There total 4 articles about (1R,4S,6R)-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: 89.0%

: 951396-67-1
(4S,6R)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-one

: 951396-65-9
(1R,4S,6R)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-ol

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

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In methanol; dichloromethane; at -78 ℃;
DOI:10.1016/j.tetlet.2007.07.042

Reference yield:

: 951396-66-0
C₂₇H₃₈O₅Si

: 951396-65-9
(1R,4S,6R)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 75 percent / PCC; NaOAc / 1,2-dichloro-ethane / 60 °C

2: 89 percent / NaBH₄; CeCl₃*7H₂O / methanol; CH₂Cl₂ / -78 °C

With sodium tetrahydroborate; cerium(III) chloride; sodium acetate; pyridinium chlorochromate; In methanol; dichloromethane; 1,2-dichloro-ethane; 2: Luche reduction;
DOI:10.1016/j.tetlet.2007.07.042

Reference yield:

: 848611-30-3
2,3-dimethoxyphenylmagnesium bromide

: 951396-65-9
(1R,4S,6R)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 85 percent / tetrahydrofuran / -78 °C

2: 75 percent / PCC; NaOAc / 1,2-dichloro-ethane / 60 °C

3: 89 percent / NaBH₄; CeCl₃*7H₂O / methanol; CH₂Cl₂ / -78 °C

With sodium tetrahydroborate; cerium(III) chloride; sodium acetate; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; 3: Luche reduction;
DOI:10.1016/j.tetlet.2007.07.042