<(2R,3S)-2,3-(Isopropylidenedioxy)pentyl> p-Toluenesulfonate

Base Information

• Chemical Name: <(2R,3S)-2,3-(Isopropylidenedioxy)pentyl> p-Toluenesulfonate
• CAS No.: 117180-65-1
• Molecular Formula: C₁₅H₂₂O₅S
• Molecular Weight: 314.403
• Mol file: 117180-65-1.mol

Synonyms:<(2R,3S)-2,3-(Isopropylidenedioxy)pentyl> p-Toluenesulfonate

Chemical Property of <(2R,3S)-2,3-(Isopropylidenedioxy)pentyl> p-Toluenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <(2R,3S)-2,3-(Isopropylidenedioxy)pentyl> p-Toluenesulfonate

There total 10 articles about <(2R,3S)-2,3-(Isopropylidenedioxy)pentyl> p-Toluenesulfonate 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%

(2R,3R)-(+)-1-(Tosyloxy)-2,3-epoxypentan (117120-70-4) + acetone (67-64-1) → <(2R,3S)-2,3-(Isopropylidenedioxy)pentyl> p-Toluenesulfonate (117180-65-1)

Guidance literature:

With aluminium trichloride; for 0.5h; Ambient temperature;

Reference yield: 95.0%

(2R,3S)-2,3-(isopropylidenedioxy)-1-pentanol (111319-80-3) + p-toluenesulfonyl chloride (98-59-9) → <(2R,3S)-2,3-(Isopropylidenedioxy)pentyl> p-Toluenesulfonate (117180-65-1)

Guidance literature:

With pyridine; In dichloromethane; at 4 ℃; for 16h;

DOI:10.1055/s-1991-26502

Reference yield:

(2S,3S)-1-Phenylthio-2,3-pentanediol (135444-87-0) → <(2R,3S)-2,3-(Isopropylidenedioxy)pentyl> p-Toluenesulfonate (117180-65-1)

Guidance literature:

Multi-step reaction with 4 steps

1: TsOH*H₂O / acetone / 12 h / Ambient temperature

2: 95 percent / MCPBA / CH₂Cl₂ / 0.33 h / 10 °C

3: 1.) NaOAc/Ac₂O 2.) NaBH₄, 1N-NaOH / 1.) reflux, 2.5 h 2.) aq. EtOH, r.t., 2 h

4: 95 percent / pyridine / CH₂Cl₂ / 16 h / 4 °C

With pyridine; sodium hydroxide; sodium tetrahydroborate; sodium acetate; acetic anhydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetone;

DOI:10.1055/s-1991-26502

upstream raw materials:

(2R,3S)-2,3-(isopropylidenedioxy)-1-pentanol

p-toluenesulfonyl chloride

(2R,3R)-(+)-1-(Tosyloxy)-2,3-epoxypentan

acetone

Downstream raw materials:

(2R,3S)-(+)-1-(Tosyloxy)-2,3-pentandiol

(2S,4R,5S)-(+)-5-Ethyl-2-methyl-2-<2-(phenylsulfonyl)ethyl>-4-(tosyloxymethyl)-1,3-dioxolan