(2S,5S)-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran-2-carbonitrile

Base Information

Chemical Name:(2S,5S)-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran-2-carbonitrile
CAS No.:149099-13-8
Molecular Formula:C₂₂H₂₇NO₂Si
Molecular Weight:365.547
Hs Code.:

Synonyms:(2S,5S)-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran-2-carbonitrile

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Chemical Property of (2S,5S)-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran-2-carbonitrile

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Technology Process of (2S,5S)-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran-2-carbonitrile

There total 4 articles about (2S,5S)-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran-2-carbonitrile 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: 37.0%

: 7677-24-9
trimethylsilyl cyanide

: 201536-71-2
1-acetoxy-2,3-dideoxy-5-O-<(1,1-dimethylethyl)diphenylsilyl>-D-glycero-pentofuranose

: 149099-13-8
(2S,5S)-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran-2-carbonitrile

: 149198-05-0
(2R,5S)-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran-2-carbonitrile

Guidance literature:: With boron trifluoride diethyl etherate; In acetonitrile; at -35 ℃; for 0.166667h;

Reference yield:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 149099-13-8
(2S,5S)-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran-2-carbonitrile

Guidance literature:: Multi-step reaction with 4 steps

1: imidazole

2: diisobutylaluminium hydride / CH₂Cl₂ / 2 h / -78 °C

3: triethylamine; DMAP / CH₂Cl₂ / 3 h

4: 1.74 g / tin(IV) chloride / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-imidazole; dmap; tin(IV) chloride; diisobutylaluminium hydride; triethylamine; In dichloromethane;
DOI:10.1021/jo016246j

Reference yield:

: 201472-26-6
(2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol

: 149099-13-8
(2S,5S)-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran-2-carbonitrile

Guidance literature:: Multi-step reaction with 2 steps

1: triethylamine; DMAP / CH₂Cl₂ / 3 h

2: 1.74 g / tin(IV) chloride / CH₂Cl₂ / 0.5 h / 0 °C

With dmap; tin(IV) chloride; triethylamine; In dichloromethane;
DOI:10.1021/jo016246j