(E)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-prop-2-en-1-ol

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Chemical Name:(E)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-prop-2-en-1-ol
CAS No.:378741-92-5
Molecular Formula:C₂₄H₃₈O₅Si
Molecular Weight:434.648
Hs Code.:

Synonyms:(E)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-prop-2-en-1-ol

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Chemical Property of (E)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-prop-2-en-1-ol

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Technology Process of (E)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-prop-2-en-1-ol

There total 2 articles about (E)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-prop-2-en-1-ol 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:

: 131311-03-0
tert-Butyl-((2R,4aR,6S,7R,8aS)-4a,6-dimethyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-dimethyl-silane

: 378741-92-5
(E)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-prop-2-en-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: OsO₄; N-methylmorpholine N-oxide / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 20 °C

1.2: NaIO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 1 h / 20 °C

2.1: potassium t-butoxide / tetrahydrofuran / 1 h / 0 - 20 °C

2.2: 6.01 g / tetrahydrofuran / 2 h / -78 - 0 °C

3.1: 5.49 g / DIBALH / CH₂Cl₂; hexane / 1 h / -78 °C

With osmium(VIII) oxide; potassium tert-butylate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; hexane; dichloromethane; water; tert-butyl alcohol; 2.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ja028167a

Reference yield:

: 374638-43-4
(2R,4aR,6R,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carbaldehyde

: 378741-92-5
(E)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-prop-2-en-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium t-butoxide / tetrahydrofuran / 1 h / 0 - 20 °C

1.2: 6.01 g / tetrahydrofuran / 2 h / -78 - 0 °C

2.1: 5.49 g / DIBALH / CH₂Cl₂; hexane / 1 h / -78 °C

With potassium tert-butylate; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; 1.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ja028167a

Reference yield:

: 378741-92-5
(E)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-prop-2-en-1-ol

: {(2S,3S)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-oxiranyl}-methanol

Guidance literature:: With tert.-butylhydroperoxide; 4 A molecular sieve; (-)-diethyl tartrate; titanium(IV) isopropylate; In 2,2,4-trimethylpentane; dichloromethane; at -28 ℃; for 20h;
DOI:10.1021/ol0166597