(R)-2,2-Dimethyl-4-((E)-3-phenylsulfanylmethoxy-propenyl)-[1,3]dioxolane

Base Information

• Chemical Name: (R)-2,2-Dimethyl-4-((E)-3-phenylsulfanylmethoxy-propenyl)-[1,3]dioxolane
• CAS No.: 122410-16-6
• Molecular Formula: C₁₅H₂₀O₃S
• Molecular Weight: 280.388
• Mol file: 122410-16-6.mol

Synonyms:(R)-2,2-Dimethyl-4-((E)-3-phenylsulfanylmethoxy-propenyl)-[1,3]dioxolane

Chemical Property of (R)-2,2-Dimethyl-4-((E)-3-phenylsulfanylmethoxy-propenyl)-[1,3]dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2,2-Dimethyl-4-((E)-3-phenylsulfanylmethoxy-propenyl)-[1,3]dioxolane

There total 5 articles about (R)-2,2-Dimethyl-4-((E)-3-phenylsulfanylmethoxy-propenyl)-[1,3]dioxolane 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: 57.0%

phenylthiomethyl chloride (7205-91-6) + (R,E)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)prop-2-en-1-ol (106757-57-7) → (R)-2,2-Dimethyl-4-((E)-3-phenylsulfanylmethoxy-propenyl)-[1,3]dioxolane (122410-16-6)

Guidance literature:

With potassium hydride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)82180-2

Reference yield: 56.0%

phenylthiomethyl chloride (7205-91-6) + (2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol (79060-23-4) → (4S)-2,2-dimethyl-4-<(E)-3-(phenylthiomethoxy)-1-propenyl>-1,3-dioxolane (122410-16-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In toluene; at 150 ℃; for 4.7h;

Reference yield:

4,5-O-isopropylidene-L-arabinose dibenzyl thioacetal (97776-79-9) → (R)-2,2-Dimethyl-4-((E)-3-phenylsulfanylmethoxy-propenyl)-[1,3]dioxolane (122410-16-6)

Guidance literature:

Multi-step reaction with 4 steps

1: Pb(OAc)4 / CH₂Cl₂

2: 1.) K₂CO₃ / H₂O

3: 95 percent / iBu₂AlH / tetrahydrofuran

4: 57 percent / KH / tetrahydrofuran

With lead(IV) acetate; potassium hydride; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)82180-2

upstream raw materials:

phenylthiomethyl chloride

(2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol

(R,E)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)prop-2-en-1-ol

4,5-O-isopropylidene-L-arabinose dibenzyl thioacetal

Downstream raw materials:

(R)-4-((E)-3-Benzenesulfonylmethoxy-propenyl)-2,2-dimethyl-[1,3]dioxolane