25320-59-6

Basic information

• Product Name: 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylchloride
• Synonyms: 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylchloride;2,3,4,6-Tetrakis-O-(phenylMethyl)-α-D-glucopyranosyl Chloride
• CAS NO: 25320-59-6
• Molecular Formula: C₃₄H₃₅ClO₅
• Molecular Weight: 559.09
• Product Categories: Carbohydrates & Derivatives
• Mol File: 25320-59-6.mol
• Article Data: 47

Chemical Properties

• Boiling Point: 663.284°C at 760 mmHg
• Flash Point: 171.477°C
• Appearance: /
• Density: 1.225g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.612
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Stability: Moisture and Temperature Sensitive
• CAS DataBase Reference: 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylchloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylchloride(25320-59-6)
• EPA Substance Registry System: 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylchloride(25320-59-6)

Safety Data

• Hazardous Substances Data: 25320-59-6(Hazardous Substances Data)

Usage

Description

2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylchloride, also known as Chloro 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranoside (CAS# 25320-59-6), is a pale yellow oil compound with significant utility in organic synthesis. It is a derivative of a-D-glucopyranosylchloride, featuring a chloro group and four benzyl groups attached to the 2, 3, 4, and 6 positions of the glucopyranosyl ring. This structural modification enhances its reactivity and compatibility with various organic reactions, making it a valuable intermediate in the synthesis of complex organic molecules.

Uses

Used in Organic Synthesis:
2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylchloride is used as a synthetic intermediate for the preparation of various complex organic molecules, particularly in the fields of pharmaceuticals, agrochemicals, and materials science. Its unique structure allows for selective functionalization and modification, enabling the synthesis of a wide range of target compounds with diverse applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylchloride is used as a key building block for the development of novel drug candidates. Its ability to participate in various organic reactions, such as glycosylation and nucleophilic substitution, makes it a versatile starting material for the synthesis of bioactive compounds with potential therapeutic applications.
Used in Agrochemical Industry:
2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylchloride is also utilized in the agrochemical industry for the synthesis of bioactive molecules with potential applications as pesticides, herbicides, or plant growth regulators. Its structural diversity and reactivity enable the development of new agrochemicals with improved efficacy and selectivity.
Used in Materials Science:
In the field of materials science, 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylchloride can be employed as a precursor for the synthesis of novel polymers, dendrimers, or other advanced materials with unique properties. Its ability to undergo various organic reactions allows for the creation of materials with tailored properties, such as enhanced mechanical strength, thermal stability, or biocompatibility.

InChI:InChI=1/C34H35ClO5/c35-34-33(39-24-29-19-11-4-12-20-29)32(38-23-28-17-9-3-10-18-28)31(37-22-27-15-7-2-8-16-27)30(40-34)25-36-21-26-13-5-1-6-14-26/h1-20,30-34H,21-25H2/t30?,31-,32+,33+,34+/m1/s1

Upstream product

• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 81342-44-1 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 115969-49-8 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 81336-89-2 (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triol 
• 117253-13-1 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 67-56-1 methanol 
• 38768-84-2 Dibenzyl(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)phosphat 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 87908-20-1 2-methoxyethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 67525-68-2 4'-Methoxyphenyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 75-36-5 acetyl chloride 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 

Downstream Products

• 70893-32-2 2-benzothiazolyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 122204-35-7 methyl 4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-galactopyranoside 
• 122204-36-8 methyl 4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-β-D-galactopyranoside 
• 117149-98-1 methyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside 
• 93414-71-2 2'-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)furan 
• 93414-72-3 (1R)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-C-(2-thienyl)-D-glucitol 
• 111277-85-1 2-[(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)oxy]pyridine 
• 119645-01-1 Acetic acid (4aR,6S,7R,8S,8aR)-6-methoxy-2-phenyl-7-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 82300-67-2 1-deoxy-1-(C-2',4',6'-trimethoxyphenyl) 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 115969-49-8 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 117253-13-1 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 82805-17-2 methyl hepta-O-benzyl-β-cellobioside 
• 82805-15-0 C₆₂H₆₆O₁₁ 
• 135080-50-1 (1α,4aβ,8α,8aα)-Decahydro-8-hydroxy-1-naphthyl 2,3,4,6-Tetra-O-benzyl-α-D-Glucopyranoside 

Relevant articles and documents

A convenient synthesis of glycosyl chlorides from sugar hemiacetals using triphosgene as the chlorine source

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Method for preparing halogenated sugar under mild conditions

The invention discloses a method for preparing halogenated sugar under mild conditions. The method comprises the following steps that an easily-prepared thioglycoside donor and a halogen simple substance or halogen intercompound undergo a reaction at room temperature to obtain the halogenated sugar (chlorine, bromine and iodine). The halogen simple substance or the halogen intercompound is commercial easily available iodine elementary substance, iodine bromide and iodine chloride. The method is suitable for various pyranoses and furanoses. The method has no limitation on a protecting group ofthe thioglycoside donor, and the protecting group can be an electron withdrawing group such as acetyl, benzoyl and the like, and can also be an electron donating group such as benzyl, silicon base andthe like. Meanwhile, the reaction can occur in various organic solvents such as dichloromethane, acetonitrile and methylbenzene. The preparation method of the halogenated sugar is simple, reaction conditions are mild, raw materials are easy to obtain, the application range is wide, the halogenated sugar is compatible with acid-labile groups such as isopropylidene ketal and silicon groups, and a pure product can be obtained by removing a solvent from the halogenated sugar which is not stable in the separation process.