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

Base Information

Chemical Name:(1S)-1-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-(benzoyloxy)ethyl methanesulfonate
CAS No.:945954-03-0
Molecular Formula:C₃₆H₄₄O₉SSi
Molecular Weight:680.891
Hs Code.:

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

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

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

There total 7 articles about (1S)-1-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-(benzoyloxy)ethyl methanesulfonate 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: 78.0%

: 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

: 124-63-0
methanesulfonyl chloride

: 945954-03-0
(1S)-1-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-(benzoyloxy)ethyl methanesulfonate

Guidance literature:: With pyridine; dmap; at 20 ℃; for 28h;
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

: 945954-03-0
(1S)-1-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-(benzoyloxy)ethyl methanesulfonate

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 78 percent / pyridine; 4-(dimethylamino)pyridine / 28 h / 20 °C

With pyridine; dmap; 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

: 945954-03-0
(1S)-1-[(1R,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-1-yl]-2-(benzoyloxy)ethyl methanesulfonate

Guidance literature:: Multi-step reaction with 7 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

7.1: 78 percent / pyridine; 4-(dimethylamino)pyridine / 28 h / 20 °C

With pyridine; dmap; 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