(E)-4-[(2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl]-2-methyl-but-2-en-1-ol

Base Information

Chemical Name:(E)-4-[(2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl]-2-methyl-but-2-en-1-ol
CAS No.:486395-02-2
Molecular Formula:C₂₅H₄₀O₅Si
Molecular Weight:448.675
Hs Code.:

Synonyms:(E)-4-[(2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl]-2-methyl-but-2-en-1-ol

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Chemical Property of (E)-4-[(2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl]-2-methyl-but-2-en-1-ol

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Technology Process of (E)-4-[(2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl]-2-methyl-but-2-en-1-ol

There total 11 articles about (E)-4-[(2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-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: 100.0%

: 486394-75-6
(E)-4-[(2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl]-2-methyl-but-2-enoic acid ethyl ester

: 486395-02-2
(E)-4-[(2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl]-2-methyl-but-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/ja028167a

Reference yield:

: (3aS,4aR,7R,8aS,10aR)-7-Phenyl-octahydro-1,4,6,8-tetraoxa-benzo[f]azulen-2-ol

: 486395-02-2
(E)-4-[(2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl]-2-methyl-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 5.93 g / toluene / 20 - 80 °C

2: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

3: 100 percent / DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

With 2,6-dimethylpyridine; diisobutylaluminium hydride; In hexane; dichloromethane; toluene; 1: Wittig reaction;
DOI:10.1021/ja028167a

Reference yield:

: 221455-78-3
2-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-ethanol

: 486395-02-2
(E)-4-[(2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl]-2-methyl-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 99 percent / I₂; PPh₃; imidazole / tetrahydrofuran / 0.33 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -20 °C

2.2: tetrahydrofuran; hexane / 1.17 h / -20 - 0 °C

3.1: 122.7 mg / tetra-butylammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

4.1: N-methylmorpholine / CH₂Cl₂ / 20 °C

5.1: 12.43 g / NaHCO₃ / acetonitrile; H₂O / 20 °C

6.1: 70 percent / SmI₂; methanol / tetrahydrofuran / 0.08 h / 20 °C

7.1: DIBALH / CH₂Cl₂; hexane / 1 h / -78 °C

8.1: 5.93 g / toluene / 20 - 80 °C

9.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

10.1: 100 percent / DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

With 4-methyl-morpholine; 1H-imidazole; 2,6-dimethylpyridine; methanol; n-butyllithium; samarium diiodide; tetrabutyl ammonium fluoride; iodine; diisobutylaluminium hydride; sodium hydrogencarbonate; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; water; toluene; acetonitrile; 8.1: Wittig reaction;
DOI:10.1021/ja028167a