a-D-Glucofuranose,1,2:5,6-bis-O-(1-methylethylidene)-3-O-(phenylmethyl)-, CAS No. 18685-18-2

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18685-18-2

Catalog No. EBD3601470

CAS 18685-18-2

Name a-D-Glucofuranose,1,2:5,6-bis-O-(1-methylethylidene)-3-O-(phenylmethyl)-

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Basic Information

Synonyms: D-Glucose,3-O-benzyl-1,2:5,6-di-O-isopropylidene-(6CI) Glucofuranose,3-O-benzyl-1,2:5,6-di-O-isopropylidene-(7CI) Glucofuranose,3-O-benzyl-1,2:5,6-di-O-isopropylidene-,a-D-(8CI) 3-O-Benzyl-1,2:5,6-di-O-isopropylidene-a-D-glucofuranose NSC56267 a-D-Glucofuranose,1,2:5,6-bis-O-(1-methylethylidene)-3-O-(phenylmethyl)- 3-O-Benzyl-1,2,5,6-di-O-isopropylidene-alpha-D-glucofuranose 3-(2,2-dimethyl-1,3-dioxolan-4-yl)-7,7-dimethyl-4-phenylmethoxy-2,6,8-trioxabicyclo[3.3.0]octane 6-(benzyloxy)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole(non-preferredname) 3-O-Benzyl-1,2 5,6-di-O-isopropylidene-α-D-glucofuranose 1,2:5,6-bis-O-(1-methylethylidene)-3-O-(phenylmethyl)-a-D-Glucofuranose 1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-Glucofuranose 3-O-benzyl-1,2:5,6-di-O-isopropylidene-D-Glucofuranose

Molecular Formula: C19H26O6

Molecular Weight: 350.41

Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Saccharides, Nucleosides, and Nucleotides Synthetic Chemistry > Organic Building Blocks > Other Organic Building Blocks

Product Description:

This compound, (3aR,5R,6aS)-6-(Benzyloxy)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole, is a protected derivative of α-D-glucofuranose. It is specifically a 1,2:5,6-bis-O-isopropylidene-3-O-benzyl derivative. The structure features multiple protecting groups: two isopropylidene (acetonide) groups and one benzyl (Bn) group, rendering the sugar hydroxyls inert for selective manipulation in synthetic sequences. Its primary application is as a crucial chiral building block and advanced intermediate in synthetic organic chemistry, particularly for the synthesis of complex carbohydrates, nucleosides, and glycomimetics. The specific protection pattern makes it a valuable precursor for the stereoselective introduction of various functionalities at the remaining positions, enabling the construction of biologically active molecules. It is extensively used in medicinal chemistry research for developing glycosidase inhibitors, antiviral agents, and other therapeutics that target carbohydrate-processing pathways. As a highly functionalized and enantiomerically pure sugar derivative, it is not a commodity chemical but a specialized research chemical. Its handling requires standard precautions for organic compounds, and it should be stored under inert atmosphere at low temperatures to maintain stability.

Physical Properties

Boiling Point: 422.6 °C at 760 mmHg

Flash Point: 168.3 °C

Density: 1.21 g/cm3

Analytical Data

Appearance: Colourless syrup