(E)-4-{(2S,4S,5S,6R)-6-[(Z)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propenyl]-5-methyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl}-but-2-enal

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Chemical Name:(E)-4-{(2S,4S,5S,6R)-6-[(Z)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propenyl]-5-methyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl}-but-2-enal
CAS No.:877833-52-8
Molecular Formula:C₃₆H₅₄O₄Si₂
Molecular Weight:606.993
Hs Code.:

Synonyms:(E)-4-{(2S,4S,5S,6R)-6-[(Z)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propenyl]-5-methyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl}-but-2-enal

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Chemical Property of (E)-4-{(2S,4S,5S,6R)-6-[(Z)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propenyl]-5-methyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl}-but-2-enal

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Technology Process of (E)-4-{(2S,4S,5S,6R)-6-[(Z)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propenyl]-5-methyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl}-but-2-enal

There total 12 articles about (E)-4-{(2S,4S,5S,6R)-6-[(Z)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propenyl]-5-methyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl}-but-2-enal 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: 72.0%

: 877833-51-7
(2R,3S,4S,6S)-6-Allyl-2-[(Z)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propenyl]-3-methyl-4-triethylsilanyloxy-tetrahydro-pyran

: 107-02-8,25068-14-8
acrolein

: 877833-52-8
(E)-4-{(2S,4S,5S,6R)-6-[(Z)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propenyl]-5-methyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl}-but-2-enal

Guidance literature:: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 50 ℃; for 16h;
DOI:10.1016/j.tetlet.2005.11.156

Reference yield:

: 877833-42-6
4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-but-2-enal

: 877833-52-8
(E)-4-{(2S,4S,5S,6R)-6-[(Z)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propenyl]-5-methyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl}-but-2-enal

Guidance literature:: Multi-step reaction with 9 steps

1.1: n-BuBOTf; Et₃N / CH₂Cl₂ / 0.83 h / -55 - 0 °C

1.2: 90 percent / CH₂Cl₂ / 4 h / -70 °C

2.1: 88 percent / NaBH₄ / tetrahydrofuran; H₂O / 3.5 h / 20 °C

3.1: 80 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 12 h

4.1: 85 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

5.1: 88 percent / pyridinium p-toluenesulfonate / ethanol / 72 h / 20 °C

6.1: 55 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 0 °C

7.1: tetrahydrofuran / 1 h / -78 °C

8.1: trifluoroacetic acid / CH₂Cl₂ / 2 h / -78 °C

9.1: 72 percent / Grubbs' second-generation carbene catalyst / CH₂Cl₂ / 16 h / 50 °C

With dmap; sodium tetrahydroborate; n-BuBOTf; pyridinium p-toluenesulfonate; Dess-Martin periodane; triethylamine; trifluoroacetic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; ethanol; dichloromethane; water;
DOI:10.1016/j.tetlet.2005.11.156

Reference yield:

: 877833-53-9
4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-but-2-en-1-ol

: 877833-52-8
(E)-4-{(2S,4S,5S,6R)-6-[(Z)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propenyl]-5-methyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl}-but-2-enal

Guidance literature:: Multi-step reaction with 10 steps

1.1: 96 percent / tetrapropylammonium perruthenate; 4-methyl-morpholine-N-oxide / CH₂Cl₂ / 2 h / 0 °C

2.1: n-BuBOTf; Et₃N / CH₂Cl₂ / 0.83 h / -55 - 0 °C

2.2: 90 percent / CH₂Cl₂ / 4 h / -70 °C

3.1: 88 percent / NaBH₄ / tetrahydrofuran; H₂O / 3.5 h / 20 °C

4.1: 80 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 12 h

5.1: 85 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

6.1: 88 percent / pyridinium p-toluenesulfonate / ethanol / 72 h / 20 °C

7.1: 55 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 0 °C

8.1: tetrahydrofuran / 1 h / -78 °C

9.1: trifluoroacetic acid / CH₂Cl₂ / 2 h / -78 °C

10.1: 72 percent / Grubbs' second-generation carbene catalyst / CH₂Cl₂ / 16 h / 50 °C

With dmap; sodium tetrahydroborate; tetrapropylammonium perruthennate; n-BuBOTf; pyridinium p-toluenesulfonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; ethanol; dichloromethane; water;
DOI:10.1016/j.tetlet.2005.11.156