(1R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-2,7-dioxabicyclo[4.3.0]nonan-3-one

Base Information

Chemical Name:(1R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-2,7-dioxabicyclo[4.3.0]nonan-3-one
CAS No.:680227-27-4
Molecular Formula:C₂₄H₃₀O₄Si
Molecular Weight:410.585
Hs Code.:

Synonyms:(1R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-2,7-dioxabicyclo[4.3.0]nonan-3-one

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Chemical Property of (1R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-2,7-dioxabicyclo[4.3.0]nonan-3-one

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Technology Process of (1R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-2,7-dioxabicyclo[4.3.0]nonan-3-one

There total 8 articles about (1R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-2,7-dioxabicyclo[4.3.0]nonan-3-one 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: 79.0%

: 667421-80-9
methyl (2E)-3-[(2R,3R,5S)-5-tert-butyldiphenylsiloxymethyl-3-hydroxyoxolan-2-yl]prop-2-enoate

: 680227-27-4
(1R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-2,7-dioxabicyclo[4.3.0]nonan-3-one

Guidance literature:: methyl (2E)-3-[(2R,3R,5S)-5-tert-butyldiphenylsiloxymethyl-3-hydroxyoxolan-2-yl]prop-2-enoate; With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 1h;

With camphor-10-sulfonic acid; In benzene; for 3h; Heating;
DOI:10.3987/com-03-9952

Reference yield:

: 667421-82-1
methyl (3S)-4-tert-butyldiphenylsiloxy-3-triethylsiloxybutanoate

: 680227-27-4
(1R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-2,7-dioxabicyclo[4.3.0]nonan-3-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: DIBAL-H / toluene / 1 h / -78 °C

1.2: 94 percent / benzene / 8 h / 20 °C

2.1: 95 percent / DIBAL-H / CH₂Cl₂; toluene / 0.17 h / -78 °C

3.1: 90 percent / Ti(Oi-Pr)4; (-)-diethyl-D-tartrate; TBHP / CH₂Cl₂; 2,2,4-trimethyl-pentane / 5 h / -20 °C

4.1: DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 2 h / 20 °C

4.2: 79 percent / benzene / 8 h / 20 °C

5.1: 82 percent / CSA / methanol / 0.08 h / 0 °C

6.1: 90 percent / Ph₃P; Pd₂(dba)3*CHCl₃ / CH₂Cl₂ / 0.08 h / 20 °C

7.1: hydrogen / Pd-C / ethanol / 1 h / 20 °C

7.2: 79 percent / CSA / benzene / 3 h / Heating

With titanium(IV) isopropylate; tert.-butylhydroperoxide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium on activated charcoal; In methanol; 2,2,4-trimethylpentane; ethanol; dichloromethane; toluene; 1.2: Wittig reaction / 3.1: Sharpless asymmetric epoxydation / 4.2: Wittig reaction;
DOI:10.3987/com-03-9952

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 680227-27-4
(1R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-2,7-dioxabicyclo[4.3.0]nonan-3-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: imidazole / dimethylformamide / 0.33 h / 20 °C

1.2: 95 percent / imidazole / dimethylformamide / 0.33 h / 0 °C

2.1: DIBAL-H / toluene / 1 h / -78 °C

2.2: 94 percent / benzene / 8 h / 20 °C

3.1: 95 percent / DIBAL-H / CH₂Cl₂; toluene / 0.17 h / -78 °C

4.1: 90 percent / Ti(Oi-Pr)4; (-)-diethyl-D-tartrate; TBHP / CH₂Cl₂; 2,2,4-trimethyl-pentane / 5 h / -20 °C

5.1: DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 2 h / 20 °C

5.2: 79 percent / benzene / 8 h / 20 °C

6.1: 82 percent / CSA / methanol / 0.08 h / 0 °C

7.1: 90 percent / Ph₃P; Pd₂(dba)3*CHCl₃ / CH₂Cl₂ / 0.08 h / 20 °C

8.1: hydrogen / Pd-C / ethanol / 1 h / 20 °C

8.2: 79 percent / CSA / benzene / 3 h / Heating

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium on activated charcoal; In methanol; 2,2,4-trimethylpentane; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 2.2: Wittig reaction / 4.1: Sharpless asymmetric epoxydation / 5.2: Wittig reaction;
DOI:10.3987/com-03-9952