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

Base Information

Chemical Name:(2S)-2-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyethyl benzoate
CAS No.:945954-02-9
Molecular Formula:C₃₅H₄₂O₇Si
Molecular Weight:602.8
Hs Code.:

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

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

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

There total 7 articles about (2S)-2-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyethyl benzoate 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: 87.0%

: 945954-01-8
(2S)-2-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyethanol

: 98-88-4
benzoyl chloride

: 945954-02-9
(2S)-2-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyethyl benzoate

Guidance literature:: With pyridine; at 0 ℃; for 4.5h;
DOI:10.1016/j.tet.2007.05.041

Reference yield:

: 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

: 945954-02-9
(2S)-2-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyethyl benzoate

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / trimethyl borate; LiBH₄ / tetrahydrofuran / 3 h / 0 - 20 °C

2: 87 percent / pyridine / 4.5 h / 0 °C

With pyridine; lithium borohydride; Trimethyl borate; In tetrahydrofuran;
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

: 945954-02-9
(2S)-2-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-hydroxyethyl benzoate

Guidance literature:: Multi-step reaction with 6 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

5.1: 99 percent / trimethyl borate; LiBH₄ / tetrahydrofuran / 3 h / 0 - 20 °C

6.1: 87 percent / pyridine / 4.5 h / 0 °C

With pyridine; 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