2-(trimethylsilyl)ethoxymethyl (1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-1,3-dimethyl-6-tosyloxymethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

Base Information

Chemical Name:2-(trimethylsilyl)ethoxymethyl (1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-1,3-dimethyl-6-tosyloxymethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate
CAS No.:854490-40-7
Molecular Formula:C₂₉H₄₂O₇SSi
Molecular Weight:562.8
Hs Code.:

2-(trimethylsilyl)ethoxymethyl (1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-1,3-dimethyl-6-tosyloxymethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

Synonyms:2-(trimethylsilyl)ethoxymethyl (1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-1,3-dimethyl-6-tosyloxymethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

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Chemical Property of 2-(trimethylsilyl)ethoxymethyl (1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-1,3-dimethyl-6-tosyloxymethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

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Technology Process of 2-(trimethylsilyl)ethoxymethyl (1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-1,3-dimethyl-6-tosyloxymethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

There total 3 articles about 2-(trimethylsilyl)ethoxymethyl (1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-1,3-dimethyl-6-tosyloxymethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate 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%

: 854490-39-4
2-(trimethylsilyl)ethoxymethyl (1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-6-hydroxymethyl-1,3-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

: 98-59-9
p-toluenesulfonyl chloride

: 854490-40-7
2-(trimethylsilyl)ethoxymethyl (1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-1,3-dimethyl-6-tosyloxymethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 2.5h;
DOI:10.1021/ol0507625

Reference yield:

: 854490-38-3
(1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-6-hydroxymethyl-1,3-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

: 854490-40-7
2-(trimethylsilyl)ethoxymethyl (1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-1,3-dimethyl-6-tosyloxymethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 195 mg / triethylamine / tetrahydrofuran / 3 h / 0 °C

2: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 2.5 h / 0 °C

With dmap; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol0507625

Reference yield:

: 854490-37-2
(1S,2R,3Z,5S,6R,7S,10R,13R)-5-ethynyl-4,6-dimethyl-13-phenyl-12,14-dioxatricyclo[8.4.0.0^2,7]tetradec-3-ene-6-carboxylic acid

: 854490-40-7
2-(trimethylsilyl)ethoxymethyl (1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-1,3-dimethyl-6-tosyloxymethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: acetic acid / H₂O / 5 h / 50 °C

2: 195 mg / triethylamine / tetrahydrofuran / 3 h / 0 °C

3: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 2.5 h / 0 °C

With dmap; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol0507625