2,6-Dioxabicyclo[3.1.1]heptane

Base Information

• Chemical Name: 2,6-Dioxabicyclo[3.1.1]heptane
• CAS No.: 52964-76-8
• Molecular Formula: C5H8O2
• DSSTox Substance ID: DTXSID30592044

Synonyms:2,6-Dioxabicyclo[3.1.1]heptane;52964-76-8;SCHEMBL9539415;DTXSID30592044;2,6-dioxabicyclo-[3.1.1]heptane

Chemical Property of 2,6-Dioxabicyclo[3.1.1]heptane

Chemical Property:

• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 100.052429494
• Heavy Atom Count: 7
• Complexity: 82.1

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COC2CC1O2

Refernces

Synthesis of Substituted 2,6-Dioxabicyclo<3.1.1>heptanes. 1,3-Anhydro-2,4,6-tri-O-benzyl- and 1,3-Anhydro-2,4,6-tri-O-(p-bromobenzyl)-β-D-mannopyranose

10.1021/jo00317a030

The study investigates the synthesis and properties of substituted 2,6-dioxabicyclo[3.1.1]heptanes, specifically focusing on the compounds 1,3-anhydro-2,4,6-tri-O-benzyl-β-D-mannopyranose and 1,3-anhydro-2,4,6-tri-O-(p-bromobenzyl)-β-D-mannopyranose. These compounds are synthesized through a series of reactions involving various reagents such as dibutyltin oxide, allyl bromide, benzyl chloride, and p-bromobenzyl bromide. The synthesis process includes steps like acetylation, benzylation, and ring closure using strong bases like sodium hydride (NaH) and potassium tert-butoxide (t-BuOK). The study aims to produce these anhydro sugars as precursors for the synthesis of 1,3-mannopyranans by ring-opening polymerizations, which are of interest for their potential applications in immunological and biochemical investigations. The compounds' structures are confirmed through mass spectrometry, 1H NMR, and 13C NMR spectroscopy, and their stability and purity are assessed through various analytical techniques.

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