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1,2-O-Isopropylidene-alpha-D-xylofuranose CAS 20031-21-4

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  • Appearance: White powder
  • Assay: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: 1,2-O-Isopropylidene-alpha-D-xylofuranose Supplement
20031-21-4

Basic Info of 1,2-O-Isopropylidene-alpha-D-xylofuranose

What is 1,2-O-Isopropylidene-alpha-D-xylofuranose?

1,2-O-Isopropylidene- α- D-xylofuranose is a basic by-product of D-xylose; Utilized as chiral architectural units, such as the synthesis of carb by-products as well as nucleoside derivatives; The chain extension of derivatives was executed by Wittig reaction.

1,2-O-Isopropylidene-α-D-xylofuranose can be used to prepare 3-deoxy-1,2-O-isopropylidene-D-xylofuranose. 3-Deoxy-1,2-O-isopropylidene-D-xylofuranose is a chiral intermediate for the synthesis of atorvastatin to produce a pharmacological side chain, and it is also the key to the synthesis of many other drug intermediates.

Atorvastatin calcium tablets (Lipitor) is a hypolipidemic drug produced by Pfizer. As the world’s most prescribed cholesterol-lowering drug and the number one prescription drug, it can significantly lower LDL cholesterol and triglyceride levels.

1,2-O-Isopropylidene-alpha-D-xylofuranose Uses

1,2-O-Isopropylidene- α- D-xylofuranose is an intermediate for the synthesis of c-glycosidic ribonucleic acid and riboaldehyde.

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Application of 1,2-O-Isopropylidene-alpha-D-xylofuranose

Selective protection of the 5-hydroxyl group of 1,2-O-isopropylidene-α-D-xylofuranose with benzoyl chloride affords 5-O-benzoyl-1,2-O-isopropylidene- D-Xylofuranose. 5-O-benzoyl-1,2-O-isopropylidene-D-xylofuranose iodine reaction to obtain 5-O-benzoyl-3-iodo-1,2-D-isopropylidene- D-Xylofuranose. 5-O-benzoyl-3-iodo-1,2-D-isopropylidene-D-xylofuranose was reduced to remove the 3-iodo group to obtain 5-O-benzoyl-3-deoxy-1, 2-D-isopropylidene-D-xylofuranose. 5-O-benzoyl-3-deoxy-1,2-D-isopropylidene-D-xylofuranose was added to remove the 5-position benzoate protection to obtain 3-deoxy-1,2-O -Isopropylidene-D-xylofuranose. 3-Deoxy-1,2-O-isopropylidene-D-xylofuranose is a chiral intermediate for the synthesis of atorvastatin to produce a pharmacologically active side chain.

Preparation of 1,2-O-Isopropylidene-alpha-D-xylofuranose

D-xylose (15.0g, 0.1mol) and anhydrous copper sulfate (34.4g, 0.216mol) were added to a 500mL round-bottomed flask, then 150mL of acetone and 3mL of 98% concentrated sulfuric acid were added, and the reaction was stirred at room temperature . The mixture was yellow-green turbid. When standing, the upper layer was a pale yellow liquid, and the lower layer was a pale blue solid. The cloudy solution gradually turned yellow-brown as the reaction proceeded. The reaction was carried out for 24 h, the mixture obtained by the reaction was filtered under reduced pressure, the filter cake was light blue, the filter cake was washed with acetone, and the filtrates were combined to obtain a yellow transparent liquid. Concentrated ammonia water was added dropwise to the filtrate to pH-7.0 to neutralize the sulfuric acid. A white flocculent precipitate (NH4)2S04 was formed. (NH4)2S04 was filtered, and the filter cake was washed with acetone to obtain a colorless liquid. Combine the filtrates, spin dry in a single-necked flask with a rotary evaporator (temperature≤50°C), and concentrate to obtain a yellow-brown syrupy substance.

100 mL of 0.1 mol·L-1 dilute hydrochloric acid was added to the diacetoneidene D-xylose obtained in the previous step, and the product was insoluble. Stirring at room temperature, the solution was gradually dissolved, and the reaction was continued for 1.5 h. TLC tracking, with CH2Cl2 developing solvent. After the reaction, solid sodium bicarbonate was added to adjust the pH to 7.2-7.5, the mixture was poured into a separatory funnel, about 30 mL of ether was added, the layers were shaken, and the organic layer was bright yellow, and the layers were separated. Repeat the wash two more times until the organic phase is colorless. Use a rotary evaporator to spin dry (temperature≤50℃), and concentrate to obtain 1,2-O-isopropylidene-α-D-xylfuranose as colorless syrup.

Reference

[Chinese invention] CN201610661280.X A kind of synthetic method of 3-deoxy-1,2-O-isopropylidene-D-xylofuranose – ChemicalBook

1,2-O-Isopropylidene-alpha-D-xylofuranose – PubChem

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