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D-Glucal CAS 13265-84-4

Factory Supply D-Glucal CAS 13265-84-4 with Best Price

  • Appearance: White powder
  • Assay: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: D-Glucal Supplement
13265-84-4

Basic Info of D-Glucal

What is D-Glucal?

Glucal is a sugar aldehyde formed from glucose. It is a chemical intermediate for the synthesis of different oligosaccharides.
Utilizing Ferrier rearrangement, glucal and its by-products can be exchanged various other chemically useful sugars.

D-glucal, additionally known as D-glucose, is a pharmaceutical intermediate, which can be prepared from pentaacetylglucose through a three-step reaction. D-glucal can be utilized to prepare fluoroglycosyl-modified paclitaxel compounds.

D-Glucal Uses

D-glucal is an important component of oligosaccharide solution and solid phase synthesis.

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Preparation of D-Glucal

Compound 8 (pentaacetylglucose) (10 g, 25.6 mmol) was dissolved in dry dichloromethane (60 mL). Under ice bath conditions, a solution of hydrobromide acetic acid (33%, mass percent) (4.9 mL, 2.0 equiv.) was slowly added thereto. The reaction was carried out at room temperature for 6 hours.

After the detection reaction was completed, an ice solution of saturated sodium bicarbonate was added to the reaction system to quench the reaction, and the two-phase extraction with dichloromethane and water was used to obtain an oily compound 9 (10.1 g, yield 96%, mass percentage) Rf0.6 (PE/EA2/1), used directly in the next step.

Compound 9 (5 g, 12.16 mmol) was dissolved in acetone, and zinc powder (7.63 g, 9.6 equiv.) and saturated NaH2PO4 solution (30 mL) were added at room temperature. The reaction was carried out at room temperature for 12 hours.

After that, it was filtered, extracted with dichloromethane and saturated NaHCO3 solution, dried over anhydrous Na2SO4, and concentrated by rotary evaporation to obtain oily compound 10 (3.1 g, yield 94%, mass percentage), Rf0.3 (PE/EA5/1 ), used directly in the next step.

At room temperature, MeONa (158.75 mg, 2.94 mmol, 0.4 equiv.) was added to a methanol solution (15 mL) of compound 10 (2 g, 7.35 mmol), and the reaction was performed for 1.5 hours. After the reaction was completed, the pH was adjusted to 7.0 with H+ ion exchange resin, Filtration, rotary evaporation and concentration to obtain oily compound 11 (1 g, yield 93%, mass percentage), Rf 0.25 (DCM/MeOH 10/1), which was directly used in the next step.

Reference

  1. Glucal – WikiPedia
  2. d-Glucal – PubChem

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