[4-(tert-butyldiphenylsilanyloxy)-6-(2-methoxy-4-oxobutyl)-tetrahydro-2H-pyran-2-yl]acetonitrile

Base Information

Chemical Name:[4-(tert-butyldiphenylsilanyloxy)-6-(2-methoxy-4-oxobutyl)-tetrahydro-2H-pyran-2-yl]acetonitrile
CAS No.:850404-87-4
Molecular Formula:C₂₈H₃₇NO₄Si
Molecular Weight:479.692
Hs Code.:

Synonyms:[4-(tert-butyldiphenylsilanyloxy)-6-(2-methoxy-4-oxobutyl)-tetrahydro-2H-pyran-2-yl]acetonitrile

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Chemical Property of [4-(tert-butyldiphenylsilanyloxy)-6-(2-methoxy-4-oxobutyl)-tetrahydro-2H-pyran-2-yl]acetonitrile

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Technology Process of [4-(tert-butyldiphenylsilanyloxy)-6-(2-methoxy-4-oxobutyl)-tetrahydro-2H-pyran-2-yl]acetonitrile

There total 10 articles about [4-(tert-butyldiphenylsilanyloxy)-6-(2-methoxy-4-oxobutyl)-tetrahydro-2H-pyran-2-yl]acetonitrile 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: 85.0%

: 850404-95-4
{(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(R)-4-hydroxy-2-methoxybutyl]-tetrahydro-2H-pyran-2-yl}acetonitrile

: 850404-87-4
[4-(tert-butyldiphenylsilanyloxy)-6-(2-methoxy-4-oxobutyl)-tetrahydro-2H-pyran-2-yl]acetonitrile

Guidance literature:: With 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane; for 2h;
DOI:10.1002/anie.200462408

Reference yield:

: 850404-93-2
{(2S,4S,6S)-6-[(R)-4-benzyloxy-2-methoxybutyl]-4-hydroxytetrahydro-2H-pyran-2-yl}acetonitrile

: 850404-87-4
[4-(tert-butyldiphenylsilanyloxy)-6-(2-methoxy-4-oxobutyl)-tetrahydro-2H-pyran-2-yl]acetonitrile

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / imidazole / dimethylformamide / 72 h

2: 90 percent / BCl₃ / hexane; CH₂Cl₂ / 20 h / -78 °C

3: 85 percent / pyridinium chlorochromate; molecular sieves / CH₂Cl₂ / 2 h

With 1H-imidazole; molecular sieve; boron trichloride; pyridinium chlorochromate; In hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo0610412

Reference yield:

: 850404-89-6
(2S,3S)-2,4,6-trimethylbenzenesulfonic acid 3-(dimethylphenylsilanyl)-2-(trimethylsilanyloxy)pent-4-enyl ester

: 850404-87-4
[4-(tert-butyldiphenylsilanyloxy)-6-(2-methoxy-4-oxobutyl)-tetrahydro-2H-pyran-2-yl]acetonitrile

Guidance literature:: Multi-step reaction with 6 steps

1.1: 80 percent / TfOH / CH₂Cl₂ / 12 h / -78 °C

2.1: 87 percent / dimethylformamide / 60 h / 60 °C

3.1: mercury trifluoroacetate / tetrahydrofuran / 18 h

3.2: 76 percent / NaBH₄; NaOH / tetrahydrofuran

4.1: 95 percent / imidazole / dimethylformamide / 72 h

5.1: 90 percent / BCl₃ / hexane; CH₂Cl₂ / 20 h / -78 °C

6.1: 85 percent / pyridinium chlorochromate; molecular sieves / CH₂Cl₂ / 2 h

With 1H-imidazole; molecular sieve; trifluorormethanesulfonic acid; mercury(II) trifluoroacetate; boron trichloride; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo0610412