(2S)-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyacetic acid ethyl ester

Base Information

Chemical Name:(2S)-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyacetic acid ethyl ester
CAS No.:945953-97-9
Molecular Formula:C₃₀H₄₀O₇Si
Molecular Weight:540.729
Hs Code.:

Synonyms:(2S)-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyacetic acid ethyl ester

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Chemical Property of (2S)-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyacetic acid ethyl ester

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Technology Process of (2S)-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyacetic acid ethyl ester

There total 5 articles about (2S)-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyacetic acid ethyl ester 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: 38.0%

: 712280-94-9
{(1S,4R,6S)-1-[3',4'-(methylenedioxy)phenyl]-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexenyl}acetic acid ethyl ester

: 945953-96-8
(2R)-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyacetic acid ethyl ester

: 945953-97-9
(2S)-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyacetic acid ethyl ester

Guidance literature:: {(1S,4R,6S)-1-[3',4'-(methylenedioxy)phenyl]-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexenyl}acetic acid ethyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.75h;

With (+)-(10-camphorsulfonyl) oxaziridine; In tetrahydrofuran; at 0 ℃; for 0.75h; Further stages.;
DOI:10.1016/j.tet.2007.05.041

Reference yield:

: (4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-ol

: 945953-97-9
(2S)-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyacetic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: pyridinium chlorochromate; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 20 °C

2.1: 1.87 g / CeCl₃*7H₂O; NaBH₄ / methanol; CH₂Cl₂ / 0.5 h / -78 °C

3.1: 71 percent / 2-nitrophenol; molecular sieves 4 Angstroem / 24 h / 130 °C

4.1: LiHMDS / tetrahydrofuran / 0.75 h / 0 °C

4.2: 4 percent / (1S)-(+)-(10-camphorsulfonyl)oxaziridine / tetrahydrofuran / 0.75 h / 0 °C

With sodium tetrahydroborate; cerium(III) chloride; 4 A molecular sieve; pyridinium chlorochromate; 2-hydroxynitrobenzene; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; 2.1: Luche reduction / 3.1: Johnson-Claisen rearrangement;
DOI:10.1016/j.tet.2007.05.041

Reference yield:

: 17680-04-5
(3,4-methylenedioxy)phenylmagnesium bromide

: 945953-97-9
(2S)-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyacetic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 91 percent / tetrahydrofuran / 1 h / -100 °C

2.1: pyridinium chlorochromate; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 20 °C

3.1: 1.87 g / CeCl₃*7H₂O; NaBH₄ / methanol; CH₂Cl₂ / 0.5 h / -78 °C

4.1: 71 percent / 2-nitrophenol; molecular sieves 4 Angstroem / 24 h / 130 °C

5.1: LiHMDS / tetrahydrofuran / 0.75 h / 0 °C

5.2: 4 percent / (1S)-(+)-(10-camphorsulfonyl)oxaziridine / tetrahydrofuran / 0.75 h / 0 °C

With sodium tetrahydroborate; cerium(III) chloride; 4 A molecular sieve; pyridinium chlorochromate; 2-hydroxynitrobenzene; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; 3.1: Luche reduction / 4.1: Johnson-Claisen rearrangement;
DOI:10.1016/j.tet.2007.05.041