(1R,4R,5S)-4-(benzo[1,3]dioxol-5-yl)-5-benzyloxy-4-[(2R)-oxiran-2-yl]-2-cyclohexen-1-ol

Base Information

Chemical Name:(1R,4R,5S)-4-(benzo[1,3]dioxol-5-yl)-5-benzyloxy-4-[(2R)-oxiran-2-yl]-2-cyclohexen-1-ol
CAS No.:945954-00-7
Molecular Formula:C₂₂H₂₂O₅
Molecular Weight:366.414
Hs Code.:

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

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Chemical Property of (1R,4R,5S)-4-(benzo[1,3]dioxol-5-yl)-5-benzyloxy-4-[(2R)-oxiran-2-yl]-2-cyclohexen-1-ol

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Technology Process of (1R,4R,5S)-4-(benzo[1,3]dioxol-5-yl)-5-benzyloxy-4-[(2R)-oxiran-2-yl]-2-cyclohexen-1-ol

There total 12 articles about (1R,4R,5S)-4-(benzo[1,3]dioxol-5-yl)-5-benzyloxy-4-[(2R)-oxiran-2-yl]-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: 98.0%

: 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

: 945954-00-7
(1R,4R,5S)-4-(benzo[1,3]dioxol-5-yl)-5-benzyloxy-4-[(2R)-oxiran-2-yl]-2-cyclohexen-1-ol

Guidance literature:: (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; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 2h;

With sodium methylate; In tetrahydrofuran; methanol; at 20 ℃; for 3h; Further stages.;
DOI:10.1016/j.tet.2007.05.041

Reference yield: 93.0%

: 945953-99-1
C₃₅H₄₄O₈SiS

: 945954-00-7
(1R,4R,5S)-4-(benzo[1,3]dioxol-5-yl)-5-benzyloxy-4-[(2R)-oxiran-2-yl]-2-cyclohexen-1-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 11h;
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

: 945954-00-7
(1R,4R,5S)-4-(benzo[1,3]dioxol-5-yl)-5-benzyloxy-4-[(2R)-oxiran-2-yl]-2-cyclohexen-1-ol

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: 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

6.1: 88 percent / triethylamine / CH₂Cl₂ / 4 h / 0 - 20 °C

7.1: 93 percent / Bu₄NF / tetrahydrofuran / 11 h / 0 - 20 °C

With sodium tetrahydroborate; lithium borohydride; cerium(III) chloride; Trimethyl borate; 4 A molecular sieve; tetrabutyl ammonium fluoride; triethylamine; 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