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

Base Information

Chemical Name:(E)-4-[(4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-2-methyl-but-2-en-1-ol
CAS No.:807616-96-2
Molecular Formula:C₂₄H₃₈O₅Si
Molecular Weight:434.648
Hs Code.:

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

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

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

There total 9 articles about (E)-4-[(4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-2-methyl-but-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:

: 807617-33-0
(E)-4-[(4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-2-methyl-but-2-enoic acid ethyl ester

: 807616-96-2
(E)-4-[(4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-2-methyl-but-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In hexane; toluene; at -78 ℃; for 0.5h;
DOI:10.1021/ja0449269

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 807616-96-2
(E)-4-[(4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-2-methyl-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 170 mg / CSA / ethyl acetate / 16 h / 20 °C

2: 173 mg / N-methylmorpholine / CH₂Cl₂ / 4 h / 20 °C

3: 98 percent / NaHCO₃; MeI / acetonitrile / 22 h / 20 °C

4: 95 percent / SmI₂ / tetrahydrofuran; methanol / 0.17 h / 0 °C

5: DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

6: 3.19 g / toluene / 0.5 h / 100 °C

7: 4.47 g / imidazole / dimethylformamide / 15 h / 20 °C

8: 3.25 g / DIBAL-Hi₁₉₈ / toluene; hexane / 0.5 h / -78 °C

With 4-methyl-morpholine; 1H-imidazole; samarium diiodide; camphor-10-sulfonic acid; diisobutylaluminium hydride; sodium hydrogencarbonate; methyl iodide; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 2: hetero-Michael reaction / 6: Wittig reaction;
DOI:10.1021/ja0449269

Reference yield:

: 50907-65-8
2-deoxy-D-erythro-pentose cyclic 1,3-propanediyl mercaptal

: 807616-96-2
(E)-4-[(4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-2-methyl-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 170 mg / CSA / ethyl acetate / 16 h / 20 °C

2: 173 mg / N-methylmorpholine / CH₂Cl₂ / 4 h / 20 °C

3: 98 percent / NaHCO₃; MeI / acetonitrile / 22 h / 20 °C

4: 95 percent / SmI₂ / tetrahydrofuran; methanol / 0.17 h / 0 °C

5: DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

6: 3.19 g / toluene / 0.5 h / 100 °C

7: 4.47 g / imidazole / dimethylformamide / 15 h / 20 °C

8: 3.25 g / DIBAL-Hi₁₉₈ / toluene; hexane / 0.5 h / -78 °C

With 4-methyl-morpholine; 1H-imidazole; samarium diiodide; camphor-10-sulfonic acid; diisobutylaluminium hydride; sodium hydrogencarbonate; methyl iodide; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 2: hetero-Michael reaction / 6: Wittig reaction;
DOI:10.1021/ja0449269