(4R,6R)-4-[(2R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylprop-1-yl]-6-ethenyl-2,2,5,5-tetramethyl-1,3-dioxane

Base Information

Chemical Name:(4R,6R)-4-[(2R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylprop-1-yl]-6-ethenyl-2,2,5,5-tetramethyl-1,3-dioxane
CAS No.:366454-65-1
Molecular Formula:C₃₀H₄₄O₃Si
Molecular Weight:480.763
Hs Code.:

Synonyms:(4R,6R)-4-[(2R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylprop-1-yl]-6-ethenyl-2,2,5,5-tetramethyl-1,3-dioxane

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Chemical Property of (4R,6R)-4-[(2R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylprop-1-yl]-6-ethenyl-2,2,5,5-tetramethyl-1,3-dioxane

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Technology Process of (4R,6R)-4-[(2R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylprop-1-yl]-6-ethenyl-2,2,5,5-tetramethyl-1,3-dioxane

There total 18 articles about (4R,6R)-4-[(2R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylprop-1-yl]-6-ethenyl-2,2,5,5-tetramethyl-1,3-dioxane 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:

: 366454-86-6
(2S,4S)-4-hydroxymethyl-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxane

: 366454-65-1
(4R,6R)-4-[(2R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylprop-1-yl]-6-ethenyl-2,2,5,5-tetramethyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 10 steps

1.1: oxalyl chloride DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.67 h / 0 °C

2.2: tetrahydrofuran; hexane / 4 h / 0 °C

3.1: DIBAL-H / CH₂Cl₂ / -78 - 20 °C

4.1: oxalyl chloride DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

5.2: tetrahydrofuran; hexane / 1 h / -50 °C

6.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

7.1: SmI₂ / tetrahydrofuran; methanol / -78 - 20 °C

8.1: 99 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / 0 - 20 °C

9.1: Me₄NBH(OAc)3; AcOH / acetonitrile / 48 h / -20 °C

10.1: PPTS / CH₂Cl₂ / 18 h / 20 °C

With n-butyllithium; samarium diiodide; oxalyl dichloride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetonitrile; 1.1: Swern oxidation / 2.2: Wittig methylenation / 4.1: Swern oxidation;
DOI:10.1021/jo0503862

Reference yield:

: 366454-87-7
(2S,4S)-5,5-dimethyl-2-(4-methoxyphenyl)-1,3-dioxan-4-carboxaldehyde

: 366454-65-1
(4R,6R)-4-[(2R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylprop-1-yl]-6-ethenyl-2,2,5,5-tetramethyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 9 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.67 h / 0 °C

1.2: tetrahydrofuran; hexane / 4 h / 0 °C

2.1: DIBAL-H / CH₂Cl₂ / -78 - 20 °C

3.1: oxalyl chloride DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

4.2: tetrahydrofuran; hexane / 1 h / -50 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

6.1: SmI₂ / tetrahydrofuran; methanol / -78 - 20 °C

7.1: 99 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / 0 - 20 °C

8.1: Me₄NBH(OAc)3; AcOH / acetonitrile / 48 h / -20 °C

9.1: PPTS / CH₂Cl₂ / 18 h / 20 °C

With n-butyllithium; samarium diiodide; oxalyl dichloride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetonitrile; 1.2: Wittig methylenation / 3.1: Swern oxidation;
DOI:10.1021/jo0503862

Reference yield:

: 366454-91-3
phenyl[(2S)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropan-1-yl]sulfide

: 366454-65-1
(4R,6R)-4-[(2R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylprop-1-yl]-6-ethenyl-2,2,5,5-tetramethyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 7 steps

1.1: Oxone / tetrahydrofuran; methanol; H₂O / 24 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

2.2: tetrahydrofuran; hexane / 1 h / -50 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

4.1: SmI₂ / tetrahydrofuran; methanol / -78 - 20 °C

5.1: 99 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / 0 - 20 °C

6.1: Me₄NBH(OAc)3; AcOH / acetonitrile / 48 h / -20 °C

7.1: PPTS / CH₂Cl₂ / 18 h / 20 °C

With Oxone; n-butyllithium; samarium diiodide; pyridinium p-toluenesulfonate; Dess-Martin periodane; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetonitrile;
DOI:10.1021/jo0503862