{(1S,5R,6R)-6-[(1S)-methoxy-2-nitroethyl]-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-yloxy}(1,1-dimethylethyl)dimethylsilane

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Chemical Name:{(1S,5R,6R)-6-[(1S)-methoxy-2-nitroethyl]-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-yloxy}(1,1-dimethylethyl)dimethylsilane
CAS No.:935264-57-6
Molecular Formula:C₂₄H₃₉NO₆Si
Molecular Weight:465.662
Hs Code.:

Synonyms:{(1S,5R,6R)-6-[(1S)-methoxy-2-nitroethyl]-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-yloxy}(1,1-dimethylethyl)dimethylsilane

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Chemical Property of {(1S,5R,6R)-6-[(1S)-methoxy-2-nitroethyl]-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-yloxy}(1,1-dimethylethyl)dimethylsilane

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Technology Process of {(1S,5R,6R)-6-[(1S)-methoxy-2-nitroethyl]-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-yloxy}(1,1-dimethylethyl)dimethylsilane

There total 15 articles about {(1S,5R,6R)-6-[(1S)-methoxy-2-nitroethyl]-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-yloxy}(1,1-dimethylethyl)dimethylsilane 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: 67.0%

: 935264-74-7
(1S)-1-[(1S,2R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]-2-nitroethan-1-ol

: 333-27-7
methyl trifluoromethanesulfonate

: 935264-57-6
{(1S,5R,6R)-6-[(1S)-methoxy-2-nitroethyl]-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-yloxy}(1,1-dimethylethyl)dimethylsilane

Guidance literature:: With 2,6-di-tert-butyl-4-methylpyridine; In dichloromethane; for 72h; Heating;
DOI:10.1021/jo061456n

Reference yield:

: 176774-93-9
(5S,6S)-6-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one

: 935264-57-6
{(1S,5R,6R)-6-[(1S)-methoxy-2-nitroethyl]-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-yloxy}(1,1-dimethylethyl)dimethylsilane

Guidance literature:: Multi-step reaction with 13 steps

1: 89 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 2.5 h / 0 - 20 °C

2: 80 percent / TBHP; VO(acac)2 / benzene; toluene / 2 h / 20 °C

3: NaH / dimethylformamide / 10 h / 20 °C

4: 4-methylmorpholine-N-oxide; OsO₄ / tetrahydrofuran; H₂O / 16 h / 20 °C

5: 17.02 g / NaIO₄ / tetrahydrofuran; H₂O / 0.25 h / 20 °C

6: 76 percent / m-CPBA / hexane; ethyl acetate / 72 h / 20 °C

7: 86 percent / AcOH; NaOAc; NaI / Zn / CH₂Cl₂ / 48 h / Heating

8: 97 percent / K₂CO₃ / methanol / 2 h / 20 °C

9: 88 percent / imiazole / dimethylformamide / 96 h / 20 °C

10: 71 percent / nBu₄NHSO₄; p-TsOH*H₂O / methanol / 24 h / -20 °C

11: 95 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.25 h / -84 - 20 °C

12: 3 percent / Cu(OAc)2*H₂O; (+)-2,2'-isopropylidenebis(indano-2-oxazoline) / ethanol / 168 h / 20 °C

13: 67 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 72 h / Heating

With 1H-imidazole; tert.-butylhydroperoxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; 2,6-di-tert-butyl-4-methylpyridine; cerium(III) chloride; copper diacetate; oxalyl dichloride; bis(acetylacetonate)oxovanadium; (+)-2,2'-isopropylidenebis(indano-2-oxazoline); sodium acetate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; zinc; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene; 6: Baeyer-Villiger rearrangement / 11: Swern oxidation / 12: asymmetric Henry reaction;
DOI:10.1021/jo061456n

Reference yield:

: 935264-61-2
(1R,5S,6S)-6-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol

: 935264-57-6
{(1S,5R,6R)-6-[(1S)-methoxy-2-nitroethyl]-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-yloxy}(1,1-dimethylethyl)dimethylsilane

Guidance literature:: Multi-step reaction with 12 steps

1: 80 percent / TBHP; VO(acac)2 / benzene; toluene / 2 h / 20 °C

2: NaH / dimethylformamide / 10 h / 20 °C

3: 4-methylmorpholine-N-oxide; OsO₄ / tetrahydrofuran; H₂O / 16 h / 20 °C

4: 17.02 g / NaIO₄ / tetrahydrofuran; H₂O / 0.25 h / 20 °C

5: 76 percent / m-CPBA / hexane; ethyl acetate / 72 h / 20 °C

6: 86 percent / AcOH; NaOAc; NaI / Zn / CH₂Cl₂ / 48 h / Heating

7: 97 percent / K₂CO₃ / methanol / 2 h / 20 °C

8: 88 percent / imiazole / dimethylformamide / 96 h / 20 °C

9: 71 percent / nBu₄NHSO₄; p-TsOH*H₂O / methanol / 24 h / -20 °C

10: 95 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.25 h / -84 - 20 °C

11: 3 percent / Cu(OAc)2*H₂O; (+)-2,2'-isopropylidenebis(indano-2-oxazoline) / ethanol / 168 h / 20 °C

12: 67 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 72 h / Heating

With 1H-imidazole; tert.-butylhydroperoxide; sodium periodate; osmium(VIII) oxide; 2,6-di-tert-butyl-4-methylpyridine; copper diacetate; oxalyl dichloride; bis(acetylacetonate)oxovanadium; (+)-2,2'-isopropylidenebis(indano-2-oxazoline); sodium acetate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; zinc; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene; 5: Baeyer-Villiger rearrangement / 10: Swern oxidation / 11: asymmetric Henry reaction;
DOI:10.1021/jo061456n