2-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-ethanol

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Chemical Name:2-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-ethanol
CAS No.:457064-28-7
Molecular Formula:C₂₉H₄₂O₆Si
Molecular Weight:514.734
Hs Code.:

Synonyms:2-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-ethanol

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Chemical Property of 2-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-ethanol

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Technology Process of 2-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-ethanol

There total 1 articles about 2-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-ethanol 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: 83.0%

: 994-30-9
triethylsilyl chloride

: 342901-72-8
(2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-6-(2-hydroxy-ethyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

: 457064-28-7
2-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-ethanol

Guidance literature:: triethylsilyl chloride; (2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-6-(2-hydroxy-ethyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol; With dmap; In dichloromethane; at 0 ℃;

With pyridinium p-toluenesulfonate; In methanol; dichloromethane; at 0 ℃; Further stages.;
DOI:10.1021/ol026306n

Reference yield:

: 457064-28-7
2-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-ethanol

: 457064-29-8
(Z)-6-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-hex-4-enoic acid ethyl ester

Guidance literature:: 2-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-ethanol; With pyridine-SO₃ complex; dimethyl sulfoxide; triethylamine; In dichloromethane; at 0 ℃;

BrPh₂P(CH₂)3CO₂Et; With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 0h; Further stages.;
DOI:10.1021/ol026306n

Reference yield:

: 457064-28-7
2-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-ethanol

: 457064-09-4
(13Z,16Z)-(1S,3R,6R,8S,9R,11R)-9-Benzyloxy-6-phenyl-2,5,7,12-tetraoxa-tricyclo[9.7.0.0^3,8]octadeca-13,16-diene-13-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: SO₃*Pyr; Et₃N; DMSO / CH₂Cl₂ / 0 °C

1.2: KHMDS / tetrahydrofuran / 0 h / -78 °C

2.1: Ba(OH)2*8H₂O / dioxane; H₂O / 60 °C

2.2: 88 percent / CSA / CH₂Cl₂; methanol / 20 °C

3.1: 2,4,6-Cl₃C₆H₂COCl; Et₃N / tetrahydrofuran / 20 °C

3.2: 71 percent / DMAP / benzene / 80 °C

4.1: 6.39 g / potassium hexamethyldisilazide; hexamethylphosphoric triamide / tetrahydrofuran; toluene / 0.67 h / -78 °C

5.1: 76 percent / triethylamine / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / dimethylformamide / 15 h / 50 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; barium dihydroxide; pyridine-SO₃ complex; 2,4,6-trichlorobenzoyl chloride; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol026306n