(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate
• CAS No.: 7305-59-1
• Molecular Formula: C₁₃H₁₈O₅S
• Molecular Weight: 286.349
• European Community (EC) Number: 628-104-7
• NSC Number: 36147
• DSSTox Substance ID: DTXSID101347171
• Nikkaji Number: J686.668I
• Mol file: 7305-59-1.mol

Synonyms:7305-59-1;(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate;2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate;D,L-Tosylisopropylideneglycerol;NSC36147;NSC 36147;(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzene-1-sulfonate;Solketal Tosylate;(S)-(+)-2,2-Dimethyl-1,3-dioxolane-4-ylmethyl p-Toluenesulfonate;Thiophene,2,5-dichloro-;2,2-dimethyl-4-tosyloxymethyl-1,3-dioxolane;SCHEMBL411517;(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate #;SRKDUHUULIWXFT-UHFFFAOYSA-;DTXSID101347171;NSC-36147;AKOS015888845;SB44218;AC-28995;A4947;FT-0654231;FT-0655354;FT-0675328;E89266;EN300-12624506;2,2-dimethyl-1,3-dioxolan-4-yl-methyl p-toluensulfonate;2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluene sulfonate;2,2-Dimethyl-4-(p-toluenesulfonyloxymethyl)-1,3-dioxolane;2,2-Dimethyl[1,3]dioxolan-4-ylmethyl toluene-4-sulfonate;4-(4-toluenesulphonyloxymethyl)-2,2-dimethyl-1,3-dioxolan;2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl 4-toluene-sulphonate;2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate, 97%;rac-2,2-dimethyl-1,3-dioxolan-4-yl-methyl p-toluenesulfonate;(+/-)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate;(2,2-dimethyl-1,3-dioxolan-4-yl)methyl4-methylbenzenesulfonate;[rac]-2,2-dimethyl-1,3-dioxolan-4-yl-methyl p-toluenesulfonate;2,2-dimethyl-4-(4-methyl phenyl sulphonyloxymethyl)-1,3-dioxolane;2,2-dimethyl-4-(4-methylphenylsulphonyloxymethyl)-1,3-dioxolan;4-methyl1benzenesulfinate, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl ester;rac-toluene-4-sulfonic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester;Toluene-4-sulfonic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester;toluene-4-sulfonic acid-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-ester;InChI=1/C13H18O5S/c1-10-4-6-12(7-5-10)19(14,15)17-9-11-8-16-13(2,3)18-11/h4-7,11H,8-9H2,1-3H3

Chemical Property of (2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate

Chemical Property:

• Melting Point: 47-49oC(lit.)
• Boiling Point: 400.1±25.0 °C(Predicted)
• PSA: 70.21000
• Density: 1 +-.0.06 g/cm3(Predicted)
• LogP: 2.93260
• Solubility.: Chloroform,
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 286.08749484
• Heavy Atom Count: 19
• Complexity: 390

Purity/Quality:

99% ^*data from raw suppliers

D,L-Tosylisopropylideneglycerol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC2COC(O2)(C)C
• Uses: Protected D,L-Glycerol.

Technology Process of (2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate

There total 35 articles about (2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate 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: 100.0%

p-toluenesulfonyl chloride (98-59-9) + (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8,36543-79-0) → solketal tosylate (23737-51-1,7305-59-1)

Guidance literature:

With pyridine; dmap; for 18h; Ambient temperature;

Reference yield: 100.0%

p-toluenesulfonyl chloride (98-59-9) + 1,2-O-isopropylidene-D-glycerol (14347-78-5,36543-79-0) → (S)-1-O-tosyl-2,3-O-isopropylideneglycerol (23735-43-5,7305-59-1)

Guidance literature:

1,2-O-isopropylidene-D-glycerol; With dmap; triethylamine; In dichloromethane; at 0 ℃;

p-toluenesulfonyl chloride; at 0 - 20 ℃;

DOI:10.1021/acsmedchemlett.9b00438

Reference yield: 99.0%

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol (22323-82-6,36543-79-0) + p-toluenesulfonyl chloride (98-59-9) → (R)-2,2-dimethyl-1,3-dioxolane-4-ylmethyl p-toluenesulfonate (23788-74-1,7305-59-1)

Guidance literature:

With pyridine; at 0 - 20 ℃;

DOI:10.1016/j.tet.2012.11.087

upstream raw materials:

(S)-1-tosyloxy-2,3-propanediol

2,2-dimethoxy-propane

acetone

p-toluenesulfonyl chloride

Downstream raw materials:

(S)-2,2-Dimethyl-4-(2-methyl-3-nitro-phenoxymethyl)-[1,3]dioxolane

(R)-4-(2-Chloro-phenoxymethyl)-2,2-dimethyl-[1,3]dioxolane

N-[(2S,3R,4R,5S,6R)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxymethyl)-5-hydroxy-2-octyloxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

N-[(2S,3R,4R,5S,6R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-6-hydroxymethyl-2-octyloxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

Refernces

• 1、 Wang, Huan,Vu, Nam Duc,Chen, Guo-Rong,Métay, Estelle,Duguet, Nicolas,Lemaire, Marc. "Selective catalytic oxidation of diglycerol". supporting information. p. 1154 - 1159. Retrieved 2021/02/26.
• 2、 Lan, Chunling Blue,Auclair, Karine. "Ammonium Chloride-Promoted Rapid Synthesis of Monosubstituted Ureas under Microwave Irradiation". supporting information. p. 5135 - 5146. Retrieved 2021/10/19.