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

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

Uses

Used in Organic Synthesis:
2,3,4-tri-O-acetylpentopyranosyl chloride is used as a protecting group reagent for [the purpose of shielding reactive hydroxyl groups during selective reactions].
Used in Carbohydrate Chemistry:
2,3,4-tri-O-acetylpentopyranosyl chloride is used as a key tool for [facilitating the synthesis of complex carbohydrates and other natural products by protecting specific hydroxyl groups].
Used in Glycosylation Reactions:
2,3,4-tri-O-acetylpentopyranosyl chloride is used as a reagent for [forming glycosidic linkages in the synthesis of various carbohydrate structures].

Upstream product

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

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 
• 19200-32-9 2,3,4-tri-O-acetyl-1,5-anhydro-D-xylitol 
• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 
• 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 

Relevant articles and documents

A facile preparation of peracylated α-aldopyranosyl chlorides with thionyl chloride and tin tetrachloride

Aldopyranose peracetates react with thionyl chloride and tin tetrachloride, producing the corresponding peracylated aldopyranosyl chlorides in very good to excellent yields (88-100%) with exclusive α-anomeric selectivity and short reaction times. The use of peracylated sugars as the substrate in large scale reactions also proceeds in high yield. Crown Copyright

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%

Indium(III) triflate-mediated one-step preparation of glycosyl halides from free sugars

In(OTf)3 has been found to be an efficient catalyst for the direct conversion of reducing sugars to their respective acylated glycosyl halides in good yields under mild conditions. The glycosyl halides so obtained can be converted to alkyl glyc

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.