(4S,6S)-2,2-dimethyl-4-phenylsulfanyl-6-(triisopropylsilyloxymethyl)-1,3-dioxane

Base Information

• Chemical Name: (4S,6S)-2,2-dimethyl-4-phenylsulfanyl-6-(triisopropylsilyloxymethyl)-1,3-dioxane
• CAS No.: 122875-54-1
• Molecular Formula: C₂₂H₃₈O₃SSi
• Molecular Weight: 410.693
• Mol file: 122875-54-1.mol

Synonyms:(4S,6S)-2,2-dimethyl-4-phenylsulfanyl-6-(triisopropylsilyloxymethyl)-1,3-dioxane

Chemical Property of (4S,6S)-2,2-dimethyl-4-phenylsulfanyl-6-(triisopropylsilyloxymethyl)-1,3-dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,6S)-2,2-dimethyl-4-phenylsulfanyl-6-(triisopropylsilyloxymethyl)-1,3-dioxane

There total 10 articles about (4S,6S)-2,2-dimethyl-4-phenylsulfanyl-6-(triisopropylsilyloxymethyl)-1,3-dioxane 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:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (4S,6S)-2,2-dimethyl-4-phenylsulfanyl-6-(triisopropylsilyloxymethyl)-1,3-dioxane (122875-54-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 71 percent / lutidine / CH₂Cl₂ / -20 °C

2: 92 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

3: 85 percent / DIBAL-H / diethyl ether / -78 °C

4: trimethylsilyl triflate (TMSOTf) / CH₂Cl₂ / -78 °C

5: trimethylsilyl triflate (TMSOTf) / CH₂Cl₂ / -78 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; lutidine; diisobutylaluminium hydride; triethylamine; In diethyl ether; dichloromethane;

DOI:10.1021/jo00282a005

Reference yield:

(3S)-3-hydroxy-4-(triisopropylsilyloxy)butyric acid methyl ester (276870-05-4) → (4S,6S)-2,2-dimethyl-4-phenylsulfanyl-6-(triisopropylsilyloxymethyl)-1,3-dioxane (122875-54-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 74 percent / aq. K₂CO₃ / methanol / 1.5 h / Heating

2: 94 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / 20 °C

3: DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

4: 18.3 g / DMAP; pyridine / CH₂Cl₂ / 1.5 h / -78 °C

5: ZnCl₂ / diethyl ether; CH₂Cl₂ / 17 h / -70 °C

With pyridine; dmap; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; zinc(II) chloride; In methanol; diethyl ether; dichloromethane;

DOI:10.1039/b400242c

Reference yield:

phenylthiotrimethylsilane (4551-15-9) + (4S,6S)-4-acetoxy-2,2-dimethyl-6-(triisopropylsilyloxymethyl)-1,3-dioxane (732290-05-0) → (4S,6S)-2,2-dimethyl-4-phenylsulfanyl-6-(triisopropylsilyloxymethyl)-1,3-dioxane (122875-54-1) + (4R,6S)-2,2-dimethyl-4-phenylsulfanyl-6-(triisopropylsilyloxymethyl)-1,3-dioxane (732290-11-8)

Guidance literature:

With zinc(II) chloride; In diethyl ether; dichloromethane; at -70 ℃; for 17h;

DOI:10.1039/b400242c

upstream raw materials:

phenylthiotrimethylsilane

(4S,6S)-4-acetoxy-2,2-dimethyl-6-(triisopropylsilyloxymethyl)-1,3-dioxane

thiophenol

triisopropylsilyl chloride