[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methyl 4-methyl-benzenesulfonate

Base Information

• Chemical Name: [(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methyl 4-methyl-benzenesulfonate
• CAS No.: 121469-49-6
• Molecular Formula: C₁₅H₂₀O₅S
• Molecular Weight: 312.387
• Mol file: 121469-49-6.mol

Synonyms:[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methyl 4-methyl-benzenesulfonate

Chemical Property of [(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methyl 4-methyl-benzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methyl 4-methyl-benzenesulfonate

There total 38 articles about [(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methyl 4-methyl-benzenesulfonate 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: 95.0%

(4S,5R)-2,2-dimethyl-4-hydroxymethyl-5-vinyl-1,3-dioxolane (114817-96-8,127758-25-2,99902-67-7) + p-toluenesulfonyl chloride (98-59-9) → (4S,5R)-2,2-dimethyl-4-(p-toluenesulfonyloxy)methyl-5-vinyl-1,3-dioxolane (100017-25-2,121469-42-9,121469-48-5,121469-49-6,133814-94-5,99902-68-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 48h; optical yield given as %de;

DOI:10.1039/c2ob25099c

Reference yield: 95.0%

(S,S)-2,2-dimethyl-4-[(tert-butyldimethylsilyloxy)methyl]-5-vinyl-1,3-dioxolane (207123-21-5) + p-toluenesulfonyl chloride (98-59-9) → [(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methyl 4-methyl-benzenesulfonate (121469-49-6)

Guidance literature:

(S,S)-2,2-dimethyl-4-[(tert-butyldimethylsilyloxy)methyl]-5-vinyl-1,3-dioxolane; p-toluenesulfonyl chloride; With triethylamine; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

With dmap; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1002/ejoc.201300434

Reference yield: 94.0%

(+/-)-2,3-Epoxy-1-tosyloxypent-4-ene (121405-00-3,121405-01-4) + acetone (67-64-1) → (+/-)-2,2-Dimethyl-4-tosyloxymethyl-5-vinyl-1,3-dioxolane (99902-68-8,100017-25-2,121469-42-9,121469-48-5,121469-49-6,133814-94-5)

Guidance literature:

With aluminium trichloride; for 24h; Ambient temperature;

DOI:10.1055/s-1988-27729

upstream raw materials:

(2R)-1-O-p-tosyl-4-pentene-1,2,3-triol

2,2-dimethoxy-propane

(2R,3S)-1-O-p-tosyl-4-pentene-1,2,3-triol

(2S,3S)-1-p-toluenesulfonyl-4-buten-1,2,3-triol

Downstream raw materials:

(-)-(4S,5S)-2,2-Dimethyl-4-<2-phenylsulfonyl-3-(2-methyl-1,3-dioxolan-2-yl)propyl>-5-vinyl-1,3-dioxolane

(-)-(1S,5R,7R)-5-Methyl-3-phenylsulfonyl-7-vinyl-6,8-dioxabicyclo<3.2.1>octane

(-)-(2R,4S,5R)-2-Methyl-2-<2-(phenylsulfonyl)ethyl>-4-tosyloxymethyl-5-vinyl-1,3-dioxolane

(+/-)-2,2-Dimethyl-4-<2-phenylsulfonyl-3-(2-methyl-1,3-dioxolan-2-yl)propyl>-5-vinyl-1,3-dioxolane