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

Base Information

Chemical Name:(2R)-2-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyethanol
CAS No.:945953-98-0
Molecular Formula:C₂₈H₃₈O₆Si
Molecular Weight:498.692
Hs Code.:

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

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

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

There total 6 articles about (2R)-2-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyethanol 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%

: 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

: 945953-98-0
(2R)-2-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyethanol

Guidance literature:: With lithium borohydride; Trimethyl borate; In tetrahydrofuran; at 0 - 20 ℃; for 4h;
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

: 945953-98-0
(2R)-2-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyethanol

Guidance literature:: Multi-step reaction with 5 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: 38 percent / (1S)-(+)-(10-camphorsulfonyl)oxaziridine / tetrahydrofuran / 0.75 h / 0 °C

5.1: 90 percent / trimethyl borate; LiBH₄ / tetrahydrofuran / 4 h / 0 - 20 °C

With sodium tetrahydroborate; lithium borohydride; cerium(III) chloride; Trimethyl borate; 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

: 945953-98-0
(2R)-2-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyethanol

Guidance literature:: Multi-step reaction with 6 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: 38 percent / (1S)-(+)-(10-camphorsulfonyl)oxaziridine / tetrahydrofuran / 0.75 h / 0 °C

6.1: 90 percent / trimethyl borate; LiBH₄ / tetrahydrofuran / 4 h / 0 - 20 °C

With sodium tetrahydroborate; lithium borohydride; cerium(III) chloride; Trimethyl borate; 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