Solketal

Base Information

• Chemical Name: Solketal
• CAS No.: 100-79-8
• Deprecated CAS: 22323-83-7,36543-79-0,2263936-21-4,36543-79-0
• Molecular Formula: C6H12O3
• Molecular Weight: 132.159
• Hs Code.: 29329970
• European Community (EC) Number: 202-888-7
• ICSC Number: 0790
• NSC Number: 59720
• UNII: 3XK098O8ZW
• DSSTox Substance ID: DTXSID9021845
• Nikkaji Number: J20.693H
• Wikipedia: Solketal
• Wikidata: Q2968854
• Metabolomics Workbench ID: 131398
• ChEMBL ID: CHEMBL3342436
• Mol file: 100-79-8.mol

Synonyms:2,2-dimethyl-1,3-dioxolane-4-methanol;2,2-dimethyl-1,3-dioxolane-4-methanol, (DL)-isomer;2,2-dimethyl-1,3-dioxolane-4-methanol, (R)-isomer;2,2-dimethyl-1,3-dioxolane-4-methanol, (S)-isomer;2,2-dimethyl-1,3-dioxolane-4-methanol, monosodium salt;2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane;2,3-isopropylidene-sn-glycerol;2,3-O-isopropylideneglycerol;glycerol acetonide

Chemical Property of Solketal

Chemical Property:

• Appearance/Colour: clear colourless liquid
• Vapor Pressure: 0.164mmHg at 25°C
• Melting Point: -27℃
• Refractive Index: n20/D 1.434
• Boiling Point: 188.499 °C at 760 mmHg
• PKA: 14.20±0.10(Predicted)
• Flash Point: 80 °C
• PSA: 38.69000
• Density: 1.034 g/cm³
• LogP: 0.13020
• Storage Temp.: 2-8°C
• Solubility.: 172g/l soluble
• Water Solubility.: miscible
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 132.078644241
• Heavy Atom Count: 9
• Complexity: 101

Purity/Quality:

99.00% ^*data from raw suppliers

1,2-O-Isopropylideneglycerol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Other Solvents
• Canonical SMILES: CC1(OCC(O1)CO)C
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes.
• General Description: Solketal (isopropylideneglycerol) is a key starting material in the synthesis of protected nucleosides, serving as a precursor for the production of modified 2',3'-dideoxy-2'-hydroxymethyl nucleosides. These nucleosides are essential intermediates for constructing "Antisense" oligonucleotides, which have therapeutic potential in gene regulation and treatments for viral infections and cancer. Solketal's role underscores its importance in pharmaceutical chemistry as a versatile building block for oligonucleotide modifications.

Technology Process of Solketal

There total 50 articles about Solketal 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%

acetone (67-64-1) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8,36543-79-0)

Guidance literature:

With sulfuric acid; at 40 ℃; Reagent/catalyst;

DOI:10.1134/S1070427216100094

Reference yield: 99.0%

oxiranyl-methanol (556-52-5) + acetone (67-64-1) → (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8,36543-79-0)

Guidance literature:

erbium(III) triflate; at 20 ℃; for 48h;

DOI:10.1002/adsc.200505096

Reference yield: 96.0%

1,2-isopropyliden-3-O-allyloxycarbonyl-sn-glycerin (1333925-44-2) + 2-propanethiol (75-33-2) → allylisopropyl sulfide (50996-72-0) + carbon dioxide (124-38-9,18923-20-1) + (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8,36543-79-0)

Guidance literature:

With Roussin's red salt ester; tetrabutylammomium bromide; potassium hydride; In tetrahydrofuran; ethanol; at 40 ℃;

DOI:10.1021/ol202270g

upstream raw materials:

oxiranyl-methanol

trifluoroborane diethyl ether

acetone

glycerol

Downstream raw materials:

glyceryl tribenzoate

2,3-dihydroxypropyl hexanoate

(S)-1,2-O-isopropylidene glycerol propionate

(R)-1,2-O-isopropylidene glycerol propionate

Refernces

Synthesis of 2′,3′-Dideoxy-2′-hydroxymethyl Nucleosides

10.1007/bf00806859

The research focuses on the synthesis of protected 2',3'-dideoxy-2'-hydroxymethyl nucleosides. These nucleosides, obtained through a multi-step procedure starting from isopropylideneglycerol, can be used as building blocks for the synthesis of 2',5'-ether linked oligonucleotides. The study aims to develop modified nucleosides that can be utilized in the creation of "Antisense" oligonucleotides, which have the potential to regulate gene expression and serve as therapeutic agents for viral and cancer treatments. Key chemicals involved in the research include isopropylideneglycerol (Solketal), tosylate, cyanessigester, and various protecting groups such as MBE (monomethoxytrityl) and DPTBSi (tert-butyldiphenylsilyl). The synthesis involves multiple steps, including alkylation, cyclization, reduction, and protection, with detailed characterization of the synthesized compounds using techniques like NMR spectroscopy. The research highlights the importance of these modified nucleosides in enhancing the stability and efficacy of oligonucleotides for potential pharmaceutical applications.

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