(R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate

Base Information

• Chemical Name: (R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate
• CAS No.: 23788-74-1
• Molecular Formula: C13H18O5S
• Molecular Weight: 286.349
• Hs Code.: 29329900
• European Community (EC) Number: 628-843-5
• DSSTox Substance ID: DTXSID10946586
• Nikkaji Number: J1.075.065B
• Wikidata: Q82924200
• Mol file: 23788-74-1.mol

Synonyms:23788-74-1;(R)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate;(R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate;[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate;(R)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate;(R)-(2,2-Dimethyl-1,3-dioxolan-4-yl)-methyl 4-methylbenzenesulfonate;(R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-ylmethyl p-toluenesulfonate;D-(-)-1,2-Isopropylideneglycerol 3-(p-Toluenesulfonate);1,2-Isopropylidene-sn-glycerol 3-tosylate;D-alpha,beta-Isopropylideneglycerol-gamma-tosylate;SCHEMBL562062;(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate #;(S)-(+)-2,2-Dimethyl-1,3-dioxolane-4-ylmethyl p-Toluenesulfonate;DTXSID10946586;(r)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate;GEO-01179;AKOS005257685;CS-W021128;D2549;1-O-Tosyl-2-O,3-O-isopropylidene-D-glycerin;EN300-7403267;2,3-O-Isopropylidene-1-O-p-tolylsulfonylglycerol;W-200246;D-.alpha.,.beta.-Isopropylideneglycerol-.gamma.-tosylate;(R)-2,2-Dimethyl-1,3-dioxolane-4-ylmethyl p-toluenesulfonate;(R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-ylmethyl p-toluenesulfate;(R)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl4-methylbenzenesulfonate;(R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl toluene-4-sulfonate;(R)-(-)-(2,2-Dimethyl-1,3-di oxolan-4-yl)methyl p-toluenesulfonate;(R)-(-)-(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl p-toluenesulfonate;(R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate, 97%;(R)-toluene-4-sulfonic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester;[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 4-methylbenzene-1-sulfonate;Toluene-4-(R)-sulfonic acid 2,2-dimethyl-[1,3]dioxolan-4-yl-methyl ester;toluene-4-sulfonic acid (R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester;1,3-Dioxolane-4-methanol,2,2-dimethyl-,4-(4-methylbenzenesulfonate),(4R)-;(R)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate, >=99.0% (sum of enantiomers, GC)

Chemical Property of (R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate

Chemical Property:

• Appearance/Colour: clear yellow to light brown viscous liquid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 41-43 °C(lit.)
• Refractive Index: n20/D 1.506(lit.)
• Boiling Point: 400.089 °C at 760 mmHg
• Flash Point: 195.767 °C
• PSA: 70.21000
• Density: 1.198 g/cm³
• LogP: 2.93260
• Storage Temp.: −20°C
• Solubility.: Dichloromethane; Chloroform; Ethyl Acetate; Methanol; DMF
• 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:

98%,99%, ^*data from raw suppliers

(R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39

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
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC[C@H]2COC(O2)(C)C
• Uses: (R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate is a chiral building block. It is used to prepare the antifungal agent ketoconazole. It is also used to prepare acyclic Nucleotide Analogs Derived from 8-Azapurines with antiviral activities.

Technology Process of (R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate

There total 10 articles about (R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl 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: 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

Reference yield: 93.0%

p-toluenesulfonyl chloride (98-59-9) + 1,2-O-isopropylidene-D-glycerol (14347-78-5,36543-79-0) → (R)-2,2-dimethyl-1,3-dioxolane-4-ylmethyl p-toluenesulfonate (23788-74-1,7305-59-1)

Guidance literature:

With pyridine; at 4 ℃;

DOI:10.1248/cpb.39.607

Reference yield: 87.7%

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

Guidance literature:

upstream raw materials:

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol

p-toluenesulfonyl chloride

1,2-O-isopropylidene-D-glycerol

1,2:5,6-di-O-isopropylidene-D-mannitol

Downstream raw materials:

3-(1-methylindol-3-yl)-4-[3-((S)-2,2-dimethyl-1,3-dioxolan-4-ylmethyloxy)phenyl]-1H-pyrrole-2,5-dione

sodium o-cresolate

2-[5-({S}-(+)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-1-methyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

C₁₅H₂₀O₅

Refernces

• 1、 Guerriero, Antonio,Cuomo, Vincenzo,Vanzanella, Fortunato,Pietra, Francesco. "A Novel Glyceryl Ester (Glyceryl Dendryphiellate A), a Trinor-eremophilane (Dendryphiellin A1), and Eremophilanes (Dendryphiellin E1 and E2) from the Marine Deuteromycete Dendryphiella salina (SUTHERLAND) PUGH et NICOT". . p. 2090 - 2096. Retrieved 1990.
• 2、 González-Gil, Inés,Zian, Debora,Vázquez-Villa, Henar,Hernández-Torres, Gloria,Martínez, R. Fernando,Khiar-Fernández, Nora,Rivera, Richard,Kihara, Yasuyuki,Devesa, Isabel,Mathivanan, Sakthikumar,Del Valle, Cristina Rosell,Zambrana-Infantes, Emma,Puigdomenech, María,Cincilla, Giovanni,Sanchez-Martinez, Melchor,Rodríguez De Fonseca, Fernando,Ferrer-Montiel, Antonio V.,Chun, Jerold,López-Vales, Rubén,López-Rodríguez, María L.,Ortega-Gutiérrez, Silvia. "A Novel Agonist of the Type 1 Lysophosphatidic Acid Receptor (LPA1), UCM-05194, Shows Efficacy in Neuropathic Pain Amelioration". supporting information. p. 2372 - 2390. Retrieved 2020/01/02.
• 3、 Ramadan, El Sayed,Rasheed, Hanaa A.,El Ashry, El Sayed H.. "Synthesis and antimicrobial screening of novel 1,3-dioxolanes linked to N-5 of 5H-1,2,4-triazino[5,6-b]indole-3-thiol". . p. 1 - 10. Retrieved 2019/05/14.