(2S,4R)-4-Phenyl-[1,3,2]dioxathiolane 2-oxide

Base Information

• Chemical Name: (2S,4R)-4-Phenyl-[1,3,2]dioxathiolane 2-oxide
• CAS No.: 51267-50-6
• Molecular Formula: C₈H₈O₃S
• Molecular Weight: 184.216
• Mol file: 51267-50-6.mol

Synonyms:

Chemical Property of (2S,4R)-4-Phenyl-[1,3,2]dioxathiolane 2-oxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-4-Phenyl-[1,3,2]dioxathiolane 2-oxide

There total 5 articles about (2S,4R)-4-Phenyl-[1,3,2]dioxathiolane 2-oxide 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: 98.0%

phenylethane 1,2-diol (93-56-1) → 4-phenyl-1,3,2-dioxathiolane 2-oxide (51267-50-6,51267-51-7,90760-98-8,90760-99-9,133522-24-4,4464-74-8)

Guidance literature:

With methanesulfonic acid; diisopropyl sulfite; In toluene;

DOI:10.1080/00397919708003344

Reference yield:

styrene oxide (96-09-3) → 4-phenyl-1,3,2-dioxathiolane 2-oxide (51267-50-6,51267-51-7,90760-98-8,90760-99-9,133522-24-4,4464-74-8)

Guidance literature:

With C₁₉H₂₇NO₅^(2-)*Cu⁽²⁺⁾*(x)H₂O; sulfur dioxide; tetrabutylammomium bromide; In neat (no solvent); at 26.84 ℃; for 8h; diastereoselective reaction; Schlenk technique;

DOI:10.1002/ejic.201900594

Reference yield:

styrene oxide (96-09-3) → (2R,4R)-4-Phenyl-[1,3,2]dioxathiolane 2-oxide (4464-74-8,51267-50-6,51267-51-7,90760-98-8,90760-99-9,133522-24-4) + (2S,4R)-4-Phenyl-[1,3,2]dioxathiolane 2-oxide (4464-74-8,51267-50-6,51267-51-7,90760-98-8,90760-99-9,133522-24-4)

Guidance literature:

With C₂₅H₂₀AlCl₆NO₄; sulfur dioxide; tetra-(n-butyl)ammonium iodide; In acetonitrile; at 50 ℃; for 3h; Overall yield = 90 %; chemoselective reaction; Flow reactor;

DOI:10.1002/adsc.201600831

upstream raw materials:

phenylethane 1,2-diol

styrene oxide

Downstream raw materials:

3-hydroxy-3-phenylpropanenitrile

2-azido-2-phenylethanol

2-chloro-2-phenylethanol

1-phenyl-2-chloroethanol

Refernces

• 1、 Malwal, Satish R.,Pardeshi, Kundansingh A.,Chakrapani, Harinath. "Synthesis of Cyclic Sulfite Diesters and their Evaluation as Sulfur Dioxide (SO2) Donors". . p. 1201 - 1205. Retrieved 2020/02/04.
• 2、 White, Rick C.,Arney Jr, Benny E.,Perry, Jacob,Thompson, Nathan,Pithan, Phil M.,von Gradowski, Sebastian,Ihmels, Heiko. "Ionic Pathways in the Photochemistry of Cyclic Sulfite Esters". . p. 1656 - 1659. Retrieved 2017/03/27.