(2R,3S)-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydro-benzofuran-3-carbonitrile

Base Information

Chemical Name:(2R,3S)-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydro-benzofuran-3-carbonitrile
CAS No.:474418-76-3
Molecular Formula:C₂₀H₃₁NO₂Si
Molecular Weight:345.557
Hs Code.:

Synonyms:(2R,3S)-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydro-benzofuran-3-carbonitrile

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Chemical Property of (2R,3S)-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydro-benzofuran-3-carbonitrile

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Technology Process of (2R,3S)-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydro-benzofuran-3-carbonitrile

There total 1 articles about (2R,3S)-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydro-benzofuran-3-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: 96.0%

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 474418-74-1
(2R,3S)-4-hydroxy-2,3-dimethyl-2,3-dihydro-benzofuran-3-carbonitrile

: 474418-76-3
(2R,3S)-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydro-benzofuran-3-carbonitrile

Guidance literature:: With TEA; In dichloromethane;
DOI:10.1021/ja0277834 DOI:10.1021/ja0364118

Reference yield:

: 474418-76-3
(2R,3S)-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydro-benzofuran-3-carbonitrile

: 1-{(2R,3R)-3-[(1E,3E)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-penta-1,3-dienyl]-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydro-benzofuran-7-yl}-3-methoxy-2-methyl-4-[(Z)-phenylimino]-cyclobut-2-enol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 92 percent / NBS / tetrahydrofuran / 20 °C

2.1: DIBAL-H / CH₂Cl₂ / -78 °C

3.1: LHMDS / tetrahydrofuran / 0.5 h / 0 °C

3.2: 368 mg / tetrahydrofuran / 20 °C

4.1: DIBAL-H / CH₂Cl₂ / 2 h / -78 °C

5.1: 910 mg / imidazole / CH₂Cl₂ / 2 h / Heating

6.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: tetrahydrofuran; hexane / 1 h / -78 °C

With 1H-imidazole; N-Bromosuccinimide; n-butyllithium; diisobutylaluminium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; 3.2: Horner-Wadsworth-Emmons;
DOI:10.1021/ja0364118

Reference yield:

: 474418-76-3
(2R,3S)-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydro-benzofuran-3-carbonitrile

: 1-{(2R,3R)-3-[(Z)-(R)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pent-3-enyl]-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydro-benzofuran-7-yl}-3-methoxy-2-methyl-4-[(Z)-phenylimino]-cyclobut-2-enol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 92 percent / NBS / tetrahydrofuran / 20 °C

2.1: DIBAL-H / CH₂Cl₂ / -78 °C

3.1: TiCl₄ / CH₂Cl₂ / 0.17 h / 20 °C

4.1: 78 percent / TEA; DMAP / CH₂Cl₂ / 14 h / 20 °C

5.1: 66 percent / Grubb's catalyst / CH₂Cl₂ / 16 h / Heating

6.1: DIBAL-H / CH₂Cl₂ / 4 h / 20 °C

6.2: 62 percent / NaBH₄ / methanol / 0.5 h

7.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 5 h / 20 °C

8.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -78 °C

8.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; dmap; N-Bromosuccinimide; n-butyllithium; TEA; titanium tetrachloride; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ja0364118