1,2:5,6-bis-O-(1-methylethylidene)-α-D-Gulofuranose, CAS No. 14686-89-6

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14686-89-6

Catalog No. EBD3334438

CAS 14686-89-6

Name 1,2:5,6-bis-O-(1-methylethylidene)-α-D-Gulofuranose

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Basic Information

Synonyms: GLUCOFURANOSE DIISOPROPYLIDENEGLUCOFURANOSE DI-O-ISOPROPYLIDENE-A-D-GLUCOFURANOSE,1,2,5,6- DIACETONE-ALPHA-D-GLC DIACETONE-ALPHA-D-GLUCOSE 1,2:5,6-O-DI-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSIDE 1,2:5,6-DIISOPROPYLENE-ALPHA-D-GLUCOFURANOSE (+)-1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE

Molecular Formula: C12H20O6

Molecular Weight: 260.28

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

Product Description:

1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose, commonly known as diacetone-D-glucose, is a protected derivative of D-glucose. It features two isopropylidene (acetonide) protecting groups at the 1,2- and 5,6-positions, locking the sugar into a furanose ring conformation. This compound is a white to off-white crystalline solid. Its primary significance lies in carbohydrate chemistry and pharmaceutical synthesis. As a key chiral building block, it serves as a versatile precursor for the synthesis of various biologically active molecules, including nucleoside analogs, antiviral drugs (e.g., certain reverse transcriptase inhibitors), and other modified sugars. The acetonide groups provide excellent protection for the hydroxyl groups, allowing for selective functionalization at the remaining free 3-hydroxyl position. Due to its rigid, well-defined chiral structure, it is extensively used in asymmetric synthesis and as a starting material for complex natural products and glycoconjugates. It is a fundamental reagent in research laboratories focused on medicinal chemistry and glycoscience.

Physical Properties

Melting Point: 110-111 °C(lit.)

Boiling Point: 362.8 °C at 760 mmHg

Flash Point: 173.2 °C

Density: 1.214 g/cm3

Storage: −20°C

Analytical Data

Appearance: Off-white crystalline solid