(2S,3R,6S)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-2-[2-(furan-2-yl)ethyl]-2-methyltetrahydro-2H-pyran-3-ol

Base Information

Chemical Name:(2S,3R,6S)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-2-[2-(furan-2-yl)ethyl]-2-methyltetrahydro-2H-pyran-3-ol
CAS No.:791839-26-4
Molecular Formula:C₃₀H₄₀O₄Si
Molecular Weight:492.731
Hs Code.:

Synonyms:(2S,3R,6S)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-2-[2-(furan-2-yl)ethyl]-2-methyltetrahydro-2H-pyran-3-ol

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Chemical Property of (2S,3R,6S)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-2-[2-(furan-2-yl)ethyl]-2-methyltetrahydro-2H-pyran-3-ol

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Technology Process of (2S,3R,6S)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-2-[2-(furan-2-yl)ethyl]-2-methyltetrahydro-2H-pyran-3-ol

There total 19 articles about (2S,3R,6S)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-2-[2-(furan-2-yl)ethyl]-2-methyltetrahydro-2H-pyran-3-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:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 791839-29-7
(2S,3R,6S)-2-[2-(furan-2-yl)ethyl]-6-(2-hydroxyethyl)-2-methyltetrahydro-2H-pyran-3-ol

: 791839-26-4
(2S,3R,6S)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-2-[2-(furan-2-yl)ethyl]-2-methyltetrahydro-2H-pyran-3-ol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 4h;
DOI:10.1021/ol0483955

Reference yield:

: 777076-74-1
(R)-2-methyl-1-tert-butyldimethylsiloxy-2-cyclopentene

: 791839-26-4
(2S,3R,6S)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-2-[2-(furan-2-yl)ethyl]-2-methyltetrahydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: O₃ / CH₂Cl₂ / 0.67 h / -78 °C

1.2: 4.74 g / PPh₃ / CH₂Cl₂ / 4 h / -78 °C

2.1: 88 percent / BuLi / tetrahydrofuran; hexane / 2 h / -78 - 0 °C

3.1: Mg; I₂ / tetrahydrofuran / 2 h

3.2: 45 percent / tetrahydrofuran / 1.5 h / -40 °C

4.1: 65 percent / hexamethyldisilazane; BuLi / tetrahydrofuran; hexane / 3 h / -78 - -40 °C

5.1: DIBALH / tetrahydrofuran; hexane / 5 h / 0 °C

6.1: aq. H₂SiF₆ / acetonitrile / 5 h / 20 °C

7.1: imidazole / dimethylformamide / 4 h / 20 °C

With 1H-imidazole; n-butyllithium; fluorosilicic acid; iodine; diisobutylaluminium hydride; ozone; magnesium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ol0483955

Reference yield:

: 201420-93-1
(R)-2-methyl-2-cyclopenten-1-ol

: 791839-26-4
(2S,3R,6S)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-2-[2-(furan-2-yl)ethyl]-2-methyltetrahydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 87 percent / imidazole / dimethylformamide / 8 h / 20 °C

2.1: O₃ / CH₂Cl₂ / 0.67 h / -78 °C

2.2: 4.74 g / PPh₃ / CH₂Cl₂ / 4 h / -78 °C

3.1: 88 percent / BuLi / tetrahydrofuran; hexane / 2 h / -78 - 0 °C

4.1: Mg; I₂ / tetrahydrofuran / 2 h

4.2: 45 percent / tetrahydrofuran / 1.5 h / -40 °C

5.1: 65 percent / hexamethyldisilazane; BuLi / tetrahydrofuran; hexane / 3 h / -78 - -40 °C

6.1: DIBALH / tetrahydrofuran; hexane / 5 h / 0 °C

7.1: aq. H₂SiF₆ / acetonitrile / 5 h / 20 °C

8.1: imidazole / dimethylformamide / 4 h / 20 °C

With 1H-imidazole; n-butyllithium; fluorosilicic acid; iodine; diisobutylaluminium hydride; ozone; magnesium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 3.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ol0483955