2H-Pyran-3-ol, 6-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-2-ethenyltetrahydro-2,5 -dimethyl-, (2R,3S,5S,6S)-

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Chemical Name:2H-Pyran-3-ol, 6-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-2-ethenyltetrahydro-2,5 -dimethyl-, (2R,3S,5S,6S)-
CAS No.:924656-30-4
Molecular Formula:C28H40O3Si
Molecular Weight:452.709
Hs Code.:

Synonyms:

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Chemical Property of 2H-Pyran-3-ol, 6-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-2-ethenyltetrahydro-2,5 -dimethyl-, (2R,3S,5S,6S)-

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Technology Process of 2H-Pyran-3-ol, 6-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-2-ethenyltetrahydro-2,5 -dimethyl-, (2R,3S,5S,6S)-

There total 13 articles about 2H-Pyran-3-ol, 6-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-2-ethenyltetrahydro-2,5 -dimethyl-, (2R,3S,5S,6S)- 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:

: 908865-99-6
tert-Butyl-[(4S,5S)-4-(4-methoxy-benzyloxy)-5-methyl-6-((2S,3S)-3-methyl-3-vinyl-oxiranyl)-hexyloxy]-diphenyl-silane

: 924656-30-4
(2R,3S,5S,6S)-6-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,5-dimethyl-2-vinyl-tetrahydro-pyran-3-ol

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 - 20 ℃; for 7h;
DOI:10.1021/ja062524q

Reference yield:

: 908865-90-7
(2S,3S)-6-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-hexane-1,3-diol

: 924656-30-4
(2R,3S,5S,6S)-6-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,5-dimethyl-2-vinyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 11 steps

1.1: CSA / CH₂Cl₂ / 1 h / 20 °C

2.1: 5.99 g / DIBALH / CH₂Cl₂; hexane / 1 h / -78 - -40 °C

3.1: Et₃N / CH₂Cl₂ / 1 h / 20 °C

4.1: 675.3 mg / dimethylsulfoxide / 2.5 h / 60 °C

5.1: 90 percent / DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

6.1: 97 percent / toluene / 0.5 h / 100 °C

7.1: 100 percent / DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

8.1: 88 percent / (+)-DET; Ti(O-i-Pr)4; t-BuOOH / molecular sieves 4 Angstroem / CH₂Cl₂; decane / 1.17 h / -40 °C

9.1: SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 0.75 h / 0 °C

10.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

10.2: 7.71 g / tetrahydrofuran / 0.5 h / 0 °C

11.1: DDQ; water / CH₂Cl₂ / 7 h / 0 - 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; camphor-10-sulfonic acid; water; sodium hexamethyldisilazane; diisobutylaluminium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 4 A molecular sieve; In tetrahydrofuran; decane; hexane; dichloromethane; dimethyl sulfoxide; toluene; 6.1: Wittig reaction / 8.1: Sharpless epoxidation / 10.2: Wittig olefination;
DOI:10.1021/ja066772y

Reference yield:

: tert-Butyl-{3-[(4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propoxy}-diphenyl-silane

: 924656-30-4
(2R,3S,5S,6S)-6-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,5-dimethyl-2-vinyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 5.99 g / DIBALH / CH₂Cl₂; hexane / 1 h / -78 - -40 °C

2.1: Et₃N / CH₂Cl₂ / 1 h / 20 °C

3.1: 675.3 mg / dimethylsulfoxide / 2.5 h / 60 °C

4.1: 90 percent / DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

5.1: 97 percent / toluene / 0.5 h / 100 °C

6.1: 100 percent / DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

7.1: 88 percent / (+)-DET; Ti(O-i-Pr)4; t-BuOOH / molecular sieves 4 Angstroem / CH₂Cl₂; decane / 1.17 h / -40 °C

8.1: SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 0.75 h / 0 °C

9.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

9.2: 7.71 g / tetrahydrofuran / 0.5 h / 0 °C

10.1: DDQ; water / CH₂Cl₂ / 7 h / 0 - 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; water; sodium hexamethyldisilazane; diisobutylaluminium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 4 A molecular sieve; In tetrahydrofuran; decane; hexane; dichloromethane; dimethyl sulfoxide; toluene; 5.1: Wittig reaction / 7.1: Sharpless epoxidation / 9.2: Wittig olefination;
DOI:10.1021/ja066772y