10343-54-1

Basic information

• Product Name: 2,3,4-tri-O-acetylpentopyranosyl chloride
• CAS NO: 10343-54-1
• Molecular Formula: C₁₁H₁₅ClO₇
• Molecular Weight: 294.6856
• Mol File: 10343-54-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 330.8°C at 760 mmHg
• Flash Point: 124.2°C
• Density: 1.32g/cm³
• Vapor Pressure: 0.000162mmHg at 25°C
• Refractive Index: 1.48
• CAS DataBase Reference: 2,3,4-tri-O-acetylpentopyranosyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-tri-O-acetylpentopyranosyl chloride(10343-54-1)
• EPA Substance Registry System: 2,3,4-tri-O-acetylpentopyranosyl chloride(10343-54-1)

Safety Data

• Hazardous Substances Data: 10343-54-1(Hazardous Substances Data)

Usage

General Description

2,3,4-tri-O-acetylpentopyranosyl chloride is a chemical compound that is commonly used as a protecting group reagent in organic synthesis. It is a derivative of pentopyranosyl chloride, with acetyl groups attached to the 2nd, 3rd, and 4th carbon positions. 2,3,4-tri-O-acetylpentopyranosyl chloride is often used in the synthesis of complex carbohydrates and other natural products, as the acetyl groups help to protect reactive hydroxyl groups on the sugar molecule. This allows for selective manipulation of specific hydroxyl groups in the molecule without affecting the others. 2,3,4-tri-O-acetylpentopyranosyl chloride is commonly used in glycosylation reactions to form glycosidic linkages, and it is an important tool for chemists working in the field of carbohydrate chemistry.

Upstream product

• 10300-18-2 (2,3,4-Tri-O-acetyl-β-D-xylopyranosyl) chloride 
• 58-86-6 D-xylose 
• 75-36-5 acetyl chloride 
• 3068-31-3 1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose 
• 62446-93-9 1,2,3,4-tetra-O-acetyl-D-xylopyranose 
• 67-66-3 chloroform 
• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 
• 60-29-7 diethyl ether 
• 7446-70-0 aluminium trichloride 
• 10026-13-8 phosphorus pentachloride 

Downstream Products

• 78788-56-4 Salicylanilid-O-β-D-xylopyranosidtriacetat 
• 123395-49-3 Tetrachlorhydrochinon-1.4-bis(O-β-D-xylopyranosidtriacetat) 
• 81742-16-7 5-Bromsalicyl-4'-chloranilid-O-β-D-xylopyranosidtriacetat 
• 3152-43-0 3,4-di-O-acetyl-D-xylal 
• 15356-53-3 (2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)benzene 
• 53784-33-1 2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-xylopyranose 
• 18031-28-2 9-β-D-Xylopyranosyl-adenin 
• 18520-81-5 D-(1R)-tri-O-acetyl-1-(6-amino-purin-9-yl)-1,5-anhydro-xylitol 
• 19200-32-9 2,3,4-tri-O-acetyl-1,5-anhydro-D-xylitol 
• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 

Relevant articles and documents

-

-

Highly stereoselective synthesis of peracylated α-aldopyranosyl chlorides from aldopyranose peracetates and thionyl chloride catalyzed by BiCl3 generated in situ from the procatalyst BiOCl

Aldopyranose peracetates react with thionyl chloride and BiCl3, generated in situ from a substoichiometric amount of the procatalyst BiOCl, producing the corresponding peracylated aldopyranosyl chlorides in very good to excellent yields (82-97%

Preparation of glycosyltriazenes

O-Unprotected glycosyltriazenes are prepared for the first time by coupling of 1-anthraquinone-1-diazonium hydrogensulfate with β-glycopyranosylamines to afford 1-(anthraquinone-1-yl)-3-(β-glycopyranosyl)triazenes 3a-h. Acetylation of compounds 3 furnished the O-acetates 4a-g. The stability of triazenes 3 results from fixation of the NH proton in an intramolecular hydrogen bond to one of the anthraquinone carbonyl oxgen atoms. Treatment of triazenes 4 with tert-butyl hypochlorite afforded acetoglycosyl chlorides 6 and 1-azidoanthraquinone 7. With acetic acid the triazene 4a formed tetra-O-acetyl-D-xylopyranose 9 together with 1-aminoanthraquinone 10. WIiley-VCH Verlag GmbH, 2000.