3-O-[(1,1-dimethylethyl)diphenylsilyl]-5,6-O-(1-methylethylidene)-D-talonic acid γ-lactone 2-acetate

Base Information

• Chemical Name: 3-O-[(1,1-dimethylethyl)diphenylsilyl]-5,6-O-(1-methylethylidene)-D-talonic acid γ-lactone 2-acetate
• CAS No.: 470453-57-7
• Molecular Formula: C₂₇H₃₄O₇Si
• Molecular Weight: 498.648
• Mol file: 470453-57-7.mol

Synonyms:3-O-[(1,1-dimethylethyl)diphenylsilyl]-5,6-O-(1-methylethylidene)-D-talonic acid γ-lactone 2-acetate

Chemical Property of 3-O-[(1,1-dimethylethyl)diphenylsilyl]-5,6-O-(1-methylethylidene)-D-talonic acid γ-lactone 2-acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-[(1,1-dimethylethyl)diphenylsilyl]-5,6-O-(1-methylethylidene)-D-talonic acid γ-lactone 2-acetate

There total 5 articles about 3-O-[(1,1-dimethylethyl)diphenylsilyl]-5,6-O-(1-methylethylidene)-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: 82.0%

2,2-dimethoxy-propane (77-76-9) + 3-O-[(1,1-dimethylethyl)diphenylsilyl]-D-talonic acid γ-lactone 2-acetate (470453-56-6) → 3-O-[(1,1-dimethylethyl)diphenylsilyl]-5,6-O-(1-methylethylidene)-D-talonic acid γ-lactone 2-acetate (470453-57-7)

Guidance literature:

With toluene-4-sulfonic acid; at 18 ℃; for 3h;

DOI:10.1071/CH02041

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 3-O-[(1,1-dimethylethyl)diphenylsilyl]-5,6-O-(1-methylethylidene)-D-talonic acid γ-lactone 2-acetate (470453-57-7)

Guidance literature:

Multi-step reaction with 5 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

5.1: 82 percent / p-toluenesulfonic acid / 3 h / 18 °C

With pyridine; 1H-imidazole; phosphoric acid; oxygen; toluene-4-sulfonic acid; ozone; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;

DOI:10.1071/CH02041

Reference yield:

(1S,6S)-2-chloro-6-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-2,4-cyclohexadien-1-ol acetate (470453-51-1) → 3-O-[(1,1-dimethylethyl)diphenylsilyl]-5,6-O-(1-methylethylidene)-D-talonic acid γ-lactone 2-acetate (470453-57-7)

Guidance literature:

Multi-step reaction with 4 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

4.1: 82 percent / p-toluenesulfonic acid / 3 h / 18 °C

With pyridine; phosphoric acid; oxygen; toluene-4-sulfonic acid; ozone; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;

DOI:10.1071/CH02041

upstream raw materials:

2,2-dimethoxy-propane

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

tert-butylchlorodiphenylsilane

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