[2-(trimethylsilyl)ethoxy]methyl (1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-6-tosyloxymethyl-1-methyl-3-(methoxymethoxymethyl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

Base Information

Chemical Name:[2-(trimethylsilyl)ethoxy]methyl (1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-6-tosyloxymethyl-1-methyl-3-(methoxymethoxymethyl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate
CAS No.:948995-33-3
Molecular Formula:C₃₁H₄₆O₉SSi
Molecular Weight:622.852
Hs Code.:

[2-(trimethylsilyl)ethoxy]methyl (1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-6-tosyloxymethyl-1-methyl-3-(methoxymethoxymethyl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

Synonyms:[2-(trimethylsilyl)ethoxy]methyl (1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-6-tosyloxymethyl-1-methyl-3-(methoxymethoxymethyl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

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Chemical Property of [2-(trimethylsilyl)ethoxy]methyl (1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-6-tosyloxymethyl-1-methyl-3-(methoxymethoxymethyl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

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Technology Process of [2-(trimethylsilyl)ethoxy]methyl (1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-6-tosyloxymethyl-1-methyl-3-(methoxymethoxymethyl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

There total 11 articles about [2-(trimethylsilyl)ethoxy]methyl (1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-6-tosyloxymethyl-1-methyl-3-(methoxymethoxymethyl)-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: 96.0%

: 948995-32-2
[2-(trimethylsilyl)ethoxy]methyl (1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-6-hydroxymethyl-1-methyl-3-(methoxymethoxymethyl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

: 98-59-9
p-toluenesulfonyl chloride

: 948995-33-3
[2-(trimethylsilyl)ethoxy]methyl (1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-6-tosyloxymethyl-1-methyl-3-(methoxymethoxymethyl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

Guidance literature:: With dmap; triethylamine; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1021/jo0708442

Reference yield:

: 948995-21-9
(2R,4S,5R)-5-[3-(tert-butyldimethylsilyloxy)propyl]-4-[(1E,3Z)-3-(methoxymethoxymethyl)-6-(trimethylsilyl)hexa-1,3-dien-5-ynyl]-2-phenyl-1,3-dioxane

: 948995-33-3
[2-(trimethylsilyl)ethoxy]methyl (1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-6-tosyloxymethyl-1-methyl-3-(methoxymethoxymethyl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

Guidance literature:: Multi-step reaction with 10 steps

1.1: 93 percent / AcOH / tetrahydrofuran; H₂O / 15 h

2.1: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

3.1: 82 percent / benzene / 15 h

4.1: 94 percent / DIBAL-H / CH₂Cl₂; toluene / 0.17 h / -78 °C

5.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 20 °C

6.1: 2,6-di-tert-butyl-4-methylphenol / toluene / 24 h / 80 °C

6.2: 322 mg / 2-methyl-2-butene; NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 2.5 h / 0 °C

7.1: 82 percent / n-Bu₄NF / tetrahydrofuran / 3 h / 0 °C

8.1: aq. AcOH / 5 h / 50 °C

9.1: 190 mg / Et₃N / tetrahydrofuran / 2 h / 0 °C

10.1: 96 percent / Et₃N; DMAP / tetrahydrofuran / 1 h / 0 °C

With dmap; 2,6-di-tert-butyl-4-methyl-phenol; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; water; toluene; benzene; 3.1: Horner-Wadsworth-Emmons reaction / 6.1: intramolecular Diels-Alder reaction;
DOI:10.1021/jo0708442

Reference yield:

: 948995-04-8
diethyl (E)-1-bromo-2-(methoxymethoxymethyl)-5-(trimethylsilyl)pent-2-en-4-ynyl phosphonate

: 948995-33-3
[2-(trimethylsilyl)ethoxy]methyl (1R,2S,4aR,5S,6R,8aS)-2-ethynyl-5-hydroxy-6-tosyloxymethyl-1-methyl-3-(methoxymethoxymethyl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

Guidance literature:: Multi-step reaction with 11 steps

1.1: 75 percent / LiHMDS; HMPA / tetrahydrofuran; hexane / -78 - 0 °C

2.1: 93 percent / AcOH / tetrahydrofuran; H₂O / 15 h

3.1: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

4.1: 82 percent / benzene / 15 h

5.1: 94 percent / DIBAL-H / CH₂Cl₂; toluene / 0.17 h / -78 °C

6.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 20 °C

7.1: 2,6-di-tert-butyl-4-methylphenol / toluene / 24 h / 80 °C

7.2: 322 mg / 2-methyl-2-butene; NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 2.5 h / 0 °C

8.1: 82 percent / n-Bu₄NF / tetrahydrofuran / 3 h / 0 °C

9.1: aq. AcOH / 5 h / 50 °C

10.1: 190 mg / Et₃N / tetrahydrofuran / 2 h / 0 °C

11.1: 96 percent / Et₃N; DMAP / tetrahydrofuran / 1 h / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; 2,6-di-tert-butyl-4-methyl-phenol; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; water; toluene; benzene; 1.1: Horner-Wadsworth-Emmons reaction / 4.1: Horner-Wadsworth-Emmons reaction / 7.1: intramolecular Diels-Alder reaction;
DOI:10.1021/jo0708442