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

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Chemical Name:tert-Butyl-dimethyl-((2R,4aR,6S,7R,8aS)-4a-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane
CAS No.:912281-33-5
Molecular Formula:C₂₂H₃₄O₄Si
Molecular Weight:390.595
Hs Code.:

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

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Chemical Property of tert-Butyl-dimethyl-((2R,4aR,6S,7R,8aS)-4a-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane

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Technology Process of tert-Butyl-dimethyl-((2R,4aR,6S,7R,8aS)-4a-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane

There total 1 articles about tert-Butyl-dimethyl-((2R,4aR,6S,7R,8aS)-4a-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane 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: 98.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: (2R,4aR,6S,7R,8aS)-4a-Methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 912281-33-5
tert-Butyl-dimethyl-((2R,4aR,6S,7R,8aS)-4a-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1016/j.tetlet.2006.07.027

Reference yield: 89.0%

: 912281-33-5
tert-Butyl-dimethyl-((2R,4aR,6S,7R,8aS)-4a-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane

: 912281-34-6
2-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol

Guidance literature:: tert-Butyl-dimethyl-((2R,4aR,6S,7R,8aS)-4a-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane; With thexylborane; In tetrahydrofuran; at 0 ℃;

With sodium hydroxide; dihydrogen peroxide;
DOI:10.1016/j.tetlet.2006.07.027

Reference yield:

: 912281-33-5
tert-Butyl-dimethyl-((2R,4aR,6S,7R,8aS)-4a-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane

: 912281-17-5
(2S,3S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-((S)-[1,3]dithian-2-yl-methoxymethoxy-methyl)-3-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 8 steps

1.1: thexylborane / tetrahydrofuran / 0 °C

1.2: 89 percent / aq. NaOH; H₂O₂

2.1: 99 percent / imidazole / dimethylformamide / 0 °C

3.1: 100 percent / H₂ / Pd(OH)2/C / 20 °C

4.1: 84 percent / KH / tetrahydrofuran / 0 - 20 °C

5.1: TMSI; HMDS / CH₂Cl₂ / 0 °C

5.2: 92 percent / K₂CO₃ / methanol / 20 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

7.1: n-BuLi / tetrahydrofuran / -78 °C

8.1: iPr₂NEt / CH₂Cl₂ / Heating

With 1H-imidazole; n-butyllithium; oxalyl dichloride; trimethylsilyl iodide; thexylborane; hydrogen; potassium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; palladium dihydroxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 6.1: Swern oxidation;
DOI:10.1016/j.tetlet.2006.07.027