(3R,5S)-Methyl 6-acetoxy-syn-3,5-(isopropylidenedioxy)-6-(p-tolylthio)hexanoate

Base Information

• Chemical Name: (3R,5S)-Methyl 6-acetoxy-syn-3,5-(isopropylidenedioxy)-6-(p-tolylthio)hexanoate
• CAS No.: 191854-41-8
• Molecular Formula: C₁₉H₂₆O₆S
• Molecular Weight: 382.478
• Mol file: 191854-41-8.mol

Synonyms:(3R,5S)-Methyl 6-acetoxy-syn-3,5-(isopropylidenedioxy)-6-(p-tolylthio)hexanoate

Chemical Property of (3R,5S)-Methyl 6-acetoxy-syn-3,5-(isopropylidenedioxy)-6-(p-tolylthio)hexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S)-Methyl 6-acetoxy-syn-3,5-(isopropylidenedioxy)-6-(p-tolylthio)hexanoate

There total 5 articles about (3R,5S)-Methyl 6-acetoxy-syn-3,5-(isopropylidenedioxy)-6-(p-tolylthio)hexanoate 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: 97.0%

acetic anhydride (108-24-7) + (+)-<3(R),5(S),S(R)>-Methyl syn-3,5-(isopropylidenedioxy)-6-(p-tolylsulfinyl)hexanoate (171523-69-6) → (3R,5S)-Methyl 6-acetoxy-syn-3,5-(isopropylidenedioxy)-6-(p-tolylthio)hexanoate (191854-41-8)

Guidance literature:

With sodium acetate; at 135 ℃; for 10h;

DOI:10.1021/jo00129a018

Reference yield:

(-)-menthyl p-toluenesulfinate (1517-82-4) → (3R,5S)-Methyl 6-acetoxy-syn-3,5-(isopropylidenedioxy)-6-(p-tolylthio)hexanoate (191854-41-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / NaH, t-BuLi / tetrahydrofuran; pentane / 0.67 h / 0 °C

2: 44 percent / DIBAL-H / tetrahydrofuran; toluene / 0.25 h / -78 °C

3: 1.) Et₂BOMe, 2.) NaBH₄ / 1.) THF, MeOH, -78 deg C, 20 min, 2.) -78 deg C, 4 h

4: 98 percent / p-TsOH / p-TsOH / acetone / 3 h / Ambient temperature

5: 97 percent / AcONa / 10 h / 135 °C

With sodium tetrahydroborate; diethyl methoxy borane; tert.-butyl lithium; sodium acetate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; toluene-4-sulfonic acid; In tetrahydrofuran; acetone; toluene; pentane;

DOI:10.1021/jo00129a018

Reference yield:

(+)-<3(R),5(S),S(R)> methyl 3,5-dihydroxy-6-(p-tolylsulfinyl) hexanoate (171523-68-5) → (3R,5S)-Methyl 6-acetoxy-syn-3,5-(isopropylidenedioxy)-6-(p-tolylthio)hexanoate (191854-41-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / p-TsOH / p-TsOH / acetone / 3 h / Ambient temperature

2: 97 percent / AcONa / 10 h / 135 °C

With sodium acetate; toluene-4-sulfonic acid; toluene-4-sulfonic acid; In acetone;

DOI:10.1021/jo00129a018

upstream raw materials:

acetic anhydride

(+)-<3(R),5(S),S(R)>-Methyl syn-3,5-(isopropylidenedioxy)-6-(p-tolylsulfinyl)hexanoate

(-)-menthyl p-toluenesulfinate

(+)-<3(R),5(S),S(R)> methyl 3,5-dihydroxy-6-(p-tolylsulfinyl) hexanoate

Downstream raw materials:

(E)-(3R,5S)-Methyl 7-phenyl-syn-3,5-(isopropylidenedioxy)heptenoate