3-O-[(1,1-dimethylethyl)diphenylsilyl]-D-talonic acid γ-lactone 2-acetate

Base Information

Chemical Name:3-O-[(1,1-dimethylethyl)diphenylsilyl]-D-talonic acid γ-lactone 2-acetate
CAS No.:470453-56-6
Molecular Formula:C₂₄H₃₀O₇Si
Molecular Weight:458.584
Hs Code.:

Synonyms:3-O-[(1,1-dimethylethyl)diphenylsilyl]-D-talonic acid γ-lactone 2-acetate

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Chemical Property of 3-O-[(1,1-dimethylethyl)diphenylsilyl]-D-talonic acid γ-lactone 2-acetate

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Technology Process of 3-O-[(1,1-dimethylethyl)diphenylsilyl]-D-talonic acid γ-lactone 2-acetate

There total 4 articles about 3-O-[(1,1-dimethylethyl)diphenylsilyl]-D-talonic acid γ-lactone 2-acetate 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: 54.0%

: 470453-55-5
(1S,2S,3S,4S)-5-chloro-3-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-5-cyclohexene-1,2,4-triol 4-acetate

: 470453-56-6
3-O-[(1,1-dimethylethyl)diphenylsilyl]-D-talonic acid γ-lactone 2-acetate

Guidance literature:: (1S,2S,3S,4S)-5-chloro-3-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-5-cyclohexene-1,2,4-triol 4-acetate; With pyridine; oxygen; ozone; In methanol; at -78 ℃; for 1h;

With sodium iodide; In methanol; at -78 ℃; for 3h;

With sodium tetrahydroborate; In methanol; at -60 - -40 ℃; for 6h;
DOI:10.1071/CH02041

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 470453-56-6
3-O-[(1,1-dimethylethyl)diphenylsilyl]-D-talonic acid γ-lactone 2-acetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: imidazole / CH₂Cl₂ / 1 h / 18 °C

1.2: 78 percent / 4-dimethylaminopyridine / pyridine / 2 h / 18 °C

2.1: 18 percent / m-CPBA / CH₂Cl₂ / 0 - 18 °C

3.1: 71 percent / aq. phosphoric acid / 40 h / 18 °C

4.1: O₃; O₂; pyridine / methanol / 1 h / -78 °C

4.2: NaI / methanol / 3 h / -78 °C

4.3: 54 percent / NaBH₄ / methanol / 6 h / -60 - -40 °C

With pyridine; 1H-imidazole; phosphoric acid; oxygen; ozone; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;
DOI:10.1071/CH02041

Reference yield:

: 470453-51-1
(1S,6S)-2-chloro-6-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-2,4-cyclohexadien-1-ol acetate

: 470453-56-6
3-O-[(1,1-dimethylethyl)diphenylsilyl]-D-talonic acid γ-lactone 2-acetate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 18 percent / m-CPBA / CH₂Cl₂ / 0 - 18 °C

2.1: 71 percent / aq. phosphoric acid / 40 h / 18 °C

3.1: O₃; O₂; pyridine / methanol / 1 h / -78 °C

3.2: NaI / methanol / 3 h / -78 °C

3.3: 54 percent / NaBH₄ / methanol / 6 h / -60 - -40 °C

With pyridine; phosphoric acid; oxygen; ozone; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;
DOI:10.1071/CH02041