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

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Chemical Name:(2R,3S,4S,6S)-6-Allyl-2-[(Z)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propenyl]-3-methyl-4-triethylsilanyloxy-tetrahydro-pyran
CAS No.:877833-51-7
Molecular Formula:C₃₅H₅₄O₃Si₂
Molecular Weight:578.983
Hs Code.:

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

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Chemical Property of (2R,3S,4S,6S)-6-Allyl-2-[(Z)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propenyl]-3-methyl-4-triethylsilanyloxy-tetrahydro-pyran

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Technology Process of (2R,3S,4S,6S)-6-Allyl-2-[(Z)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propenyl]-3-methyl-4-triethylsilanyloxy-tetrahydro-pyran

There total 11 articles about (2R,3S,4S,6S)-6-Allyl-2-[(Z)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propenyl]-3-methyl-4-triethylsilanyloxy-tetrahydro-pyran 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:

: 877833-50-6
(4S,5R,6R)-2-Allyl-6-[(Z)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propenyl]-5-methyl-tetrahydro-pyran-2,4-diol

: 617-86-7
triethylsilane

: 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

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at -78 ℃; for 2h;
DOI:10.1016/j.tetlet.2005.11.156

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 8 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

With dmap; sodium tetrahydroborate; n-BuBOTf; pyridinium p-toluenesulfonate; Dess-Martin periodane; triethylamine; trifluoroacetic acid; 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

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

Guidance literature:: Multi-step reaction with 9 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

With dmap; sodium tetrahydroborate; tetrapropylammonium perruthennate; n-BuBOTf; pyridinium p-toluenesulfonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; water;
DOI:10.1016/j.tetlet.2005.11.156