10300-18-2

Basic information

• Product Name: 2,3,4-tri-O-acetylpentopyranosyl chloride
• CAS NO: 10300-18-2
• Molecular Formula: C₁₁H₁₅ClO₇
• Molecular Weight: 294.6856
• Mol File: 10300-18-2.mol
• Article Data: 6

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(10300-18-2)
• EPA Substance Registry System: 2,3,4-tri-O-acetylpentopyranosyl chloride(10300-18-2)

Safety Data

• Hazardous Substances Data: 10300-18-2(Hazardous Substances Data)

Usage

General Description

2,3,4-tri-O-acetylpentopyranosyl chloride is a chemical compound that is derived from pentopyranose, a type of sugar. It is an acetylated form of pentopyranosyl chloride, meaning that it has three acetyl groups attached to it. 2,3,4-tri-O-acetylpentopyranosyl chloride is often used in organic synthesis as a protecting group for alcohols, meaning that it can be used to temporarily block the reactivity of alcohol groups in a molecule while other reactions are taking place, and then be removed later to reveal the original alcohol group. 2,3,4-tri-O-acetylpentopyranosyl chloride is an important reagent in carbohydrate chemistry and is used in the production of various pharmaceuticals and bioactive molecules.

Upstream product

• 3068-31-3 1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose 
• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 
• 7446-70-0 aluminium trichloride 
• 67-66-3 chloroform 
• 60-29-7 diethyl ether 
• 1233-03-0 α-D-xylopyranose tetraacetate 
• 62446-93-9 1,2,3,4-tetra-O-acetyl-D-xylopyranose 

Downstream Products

• 10343-54-1 2,3,4-tri-O-acetyl-α-D-xylopyranosyl chloride 
• 1195651-71-8 D-(1S)-1-phenyl-1,5-anhydro-xylitol 
• 119754-71-1 acetylated o-tolyl 1-thio-α-D-xylopyranoside 
• 100842-21-5 α-D-xylopyranosyl azide 
• 15356-53-3 (2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)benzene 
• 158419-78-4 1-(2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)-4-retinamidobenzene 
• 287731-90-2 triphenylmethyl 2,3,4-tri-O-acetyl-1-S-α-D-xylopyranoside 

Relevant articles and documents

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Reaction of 1,2-trans-glycosyl acetates with phosphorus pentachloride: New efficient approach to 1,2-trans-glycosyl chlorides

Reaction of phosphorus pentachloride with 1,2-trans-glycosyl esters is described. The reaction mechanism presumably involves formation of a tetrachlorophosphonium ion as one of the key reactive intermediates, which can be induced either by Lewis acids or by using acetonitrile as the reaction solvent. Two novel, efficient methods for the synthesis of the thermodynamically unstable glycosyl chlorides were developed based on this reaction.

REACTION OF GLYCOSYL HALIDES WITH BENZYL GRIGNARD REAGENTS: UNEXPECTED o-TOLYL ALKYLATION OF TETRA-O-ACETYLGLUCOPYRANOSYL BROMIDE AND DIRECT SYNTHESIS OF (β-GLYCOSYL)PHENYLMETHANES

The synthesis of (β-glycosyl)phenylmethanes by Grignard alkylation of glycosyl halides is investigated.Reaction of tetra-O-acetylglucopyranosyl bromide with benzylmagnesium chloride gave a good yield of a 3:1 mixture of 2-(β-D-glucopyranosyl)toluene and (β-glucosyl)phenylmethane.The requirement for an equatorial 2-acetoxy group and 6-acetoxymethyl group for the formation of the unexpected o-tolyl rearrangement product is explored by using xylosyl, mannosyl, and 2-deoxyglucosyl halides as substrates for the alkylation.Synthesis of (β-glucosyl)phenylmethane by alkylation of 2,3,4,6-tetra-O-benzylglucosyl bromide with benzylmagnesium chloride is also presented.