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

Base Information

• Chemical Name: (1S,2S,3S,4S)-5-chloro-3-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-5-cyclohexene-1,2,4-triol 4-acetate
• CAS No.: 470453-55-5
• Molecular Formula: C₂₄H₂₉ClO₅Si
• Molecular Weight: 461.03
• Mol file: 470453-55-5.mol

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

Chemical Property of (1S,2S,3S,4S)-5-chloro-3-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-5-cyclohexene-1,2,4-triol 4-acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3S,4S)-5-chloro-3-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-5-cyclohexene-1,2,4-triol 4-acetate

There total 5 articles about (1S,2S,3S,4S)-5-chloro-3-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-5-cyclohexene-1,2,4-triol 4-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: 71.0%

tetrahydrofuran (109-99-9,24979-97-3,77392-70-2) + [1S-(1α,2β,3β,6α)]-4-chloro-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-7-oxabicyclo[4.1.0]hept-4-en-3-ol acetate (470453-53-3) → (1S,2S,3S,4S)-5-chloro-3-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-5-cyclohexene-1,2,4-triol 4-acetate (470453-55-5) + (1S,2S,3S,6R)-4-chloro-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-6-(4'-hydroxybutoxy)-4-cyclohexene-1,3-diol 3-acetate

Guidance literature:

With phosphoric acid; at 18 ℃; for 40h;

DOI:10.1071/CH02041

Reference yield:

[1S-(1α,2β,3β,6α)]-4-chloro-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-7-oxabicyclo[4.1.0]hept-4-en-3-ol acetate (470453-53-3) → (1S,2S,3S,4S)-5-chloro-3-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-5-cyclohexene-1,2,4-triol 4-acetate (470453-55-5) + (1S,2S,3S,6R)-4,6-dichloro-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-4-cyclohexene-1,3-diol 3-acetate

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; at 18 ℃; for 24h;

DOI:10.1071/CH02041

Reference yield:

(1S,2S)-3-Chloro-cyclohexa-3,5-diene-1,2-diol (86992-79-2,98575-77-0,65986-73-4) → (1S,2S,3S,4S)-5-chloro-3-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-5-cyclohexene-1,2,4-triol 4-acetate (470453-55-5)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; phosphoric acid; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1071/CH02041

upstream raw materials:

tetrahydrofuran

[1S-(1α,2β,3β,6α)]-4-chloro-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-7-oxabicyclo[4.1.0]hept-4-en-3-ol acetate

(1S,2S)-3-Chloro-cyclohexa-3,5-diene-1,2-diol

tert-butylchlorodiphenylsilane

Downstream raw materials:

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

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