70831-94-6

Basic information

• Product Name: Bromo 2-Deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-α,β-D-glucopyranoside
• Synonyms: Bromo 2-Deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-α,β-D-glucopyranoside;2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-D-glucopyranosyl BroMide 3,4,6-Triacetate;3,4,6-Tri-O-acetyl-2-deoxy-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-D-glucopyranosyl bromide, 3,4,6-Tri-O-acetyl-1-bromo-1,2-dideoxy-2-phthalimido-D-glucopyranose
• CAS NO: 70831-94-6
• Molecular Formula: C₂₀H₂₀BrNO₉
• Molecular Weight: 498.2781
• Product Categories: Carbohydrates & Derivatives
• Mol File: 70831-94-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 124-128°C
• Boiling Point: 567.14°C at 760 mmHg
• Flash Point: 296.796°C
• Appearance: /
• Density: 1.594g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.597
• Storage Temp.: Amber Vial, -20?C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Sparingly), Dichloromethane (Slightly), Ethyl Acetate (Slightly)
• PKA: -2.57±0.20(Predicted)
• Stability: Moisture, Temperature sensitive; Stabilized with 2% CaCO3
• CAS DataBase Reference: Bromo 2-Deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-α,β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Bromo 2-Deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-α,β-D-glucopyranoside(70831-94-6)
• EPA Substance Registry System: Bromo 2-Deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-α,β-D-glucopyranoside(70831-94-6)

Safety Data

• Hazardous Substances Data: 70831-94-6(Hazardous Substances Data)

Usage

Description

Bromo 2-Deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-α,β-D-glucopyranoside is a complex organic compound that serves as a key intermediate in the synthesis of various glycosidic linkages. It is characterized by its unique structure, which includes a bromo group, a deoxy sugar moiety, a phthalimido group, and acetyl protecting groups. Bromo 2-Deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-α,β-D-glucopyranoside plays a crucial role in the development of new glycoconjugates and carbohydrate-based drugs.

Uses

Used in Pharmaceutical Industry:
Bromo 2-Deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-α,β-D-glucopyranoside is used as a synthetic intermediate for the preparation of β-D-N-acetyl glucosamine glycosidic linkages. These linkages are essential for the development of new glycoconjugates and carbohydrate-based drugs, which have potential applications in the treatment of various diseases, including cancer, infectious diseases, and inflammatory disorders.
Used in Carbohydrate Chemistry Research:
In the field of carbohydrate chemistry, Bromo 2-Deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-α,β-D-glucopyranoside serves as a valuable building block for the synthesis of complex carbohydrate structures. Its unique structure allows for the selective formation of glycosidic linkages, which is crucial for the development of new carbohydrate-based materials and the study of carbohydrate-mediated biological processes.
Used in Drug Discovery and Development:
Bromo 2-Deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-α,β-D-glucopyranoside is used as a key component in the design and synthesis of novel drug candidates. Its ability to form stable glycosidic linkages with various biologically active molecules makes it an attractive candidate for the development of new drugs with improved pharmacological properties, such as enhanced solubility, stability, and bioavailability.

InChI:InChI=1/C20H20BrNO9/c1-9(23)28-8-14-16(29-10(2)24)17(30-11(3)25)15(18(21)31-14)22-19(26)12-6-4-5-7-13(12)20(22)27/h4-7,14-18H,8H2,1-3H3/t14?,15-,16+,17+,18+/m0/s1

Upstream product

• 31505-45-0 2-deoxy-2-phthalimido-D-glucopyranose 
• 108-24-7 acetic anhydride 
• 138906-41-9 4-methoxylphenzyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranoside 
• 79528-48-6 methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 85-44-9 phthalic anhydride 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-phthalimido-2-deoxy-α-D-glucopyranose 

Downstream Products

• 76101-14-9 methyl-2-desoxy-2-phthalimido-β-D-glucopyranoside 
• 92052-15-8 Benzyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-desoxy-6-O-(3,4,6-tri-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-glucopyranosid 
• 95245-44-6 4-O-benzyl-1,2-O-benzylidene-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-L-rhamnopyranose 
• 95245-45-7 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl 4-O-benzyl-2,3-O-benzylidene-β-L-rhamnopyranoside 
• 101528-49-8 methyl 2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3-O-allyl-4-O-benzyl-α-L-rhamnopyranoside 
• 94926-38-2 Benzyl-O-(3,4,6-tri-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosid 
• 94926-37-1 Benzyl-O-(3,4,6-tri-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosid 
• 95245-40-2 3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-O-benzyl-1,2-O-benzylidene-β-L-rhamnopyranose 
• 95245-41-3 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-4-O-benzyl-2,3-O-benzylidene-β-L-rhamnopyranoside 
• 227601-51-6 allyl-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-O-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 387881-18-7 2-(2-{2-acetoxymethyl-5-acetylamino-6-benzyloxy-3-[4,5-diacetoxy-6-acetoxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-4-yloxy}-propionylamino)-propionic acid 2-trimethylsilanyl-ethyl ester 
• 503830-13-5 2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 622830-63-1 O-(2,3,4-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-6-O-(tert-butyldiphenylsilyl)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 
• 143564-40-3 5-(methoxycarbonyl)pentyl 4,6-O-benzylidene-2,3-bis-O-(2-deoxy-3,4,6-tri-O-acetyl-2-phthalimido-β-D-glucopyranosyl)-β-D-galactopyranoside 

Relevant articles and documents

UDP-GlcNAc Analogues as Inhibitors of O-GlcNAc Transferase (OGT): Spectroscopic, Computational, and Biological Studies

A series of glycomimetics of UDP-GlcNAc, in which the β-phosphate has been replaced by either an alkyl chain or a triazolyl ring and the sugar moiety has been replaced by a pyrrolidine ring, has been synthesized by the application of different click-chemistry procedures. Their affinities for human O-GlcNAc transferase (hOGT) have been evaluated and studied both spectroscopically and computationally. The binding epitopes of the best ligands have been determined in solution by means of saturation transfer difference (STD) NMR spectroscopy. Experimental, spectroscopic, and computational results are in agreement, pointing out the essential role of the binding of β-phosphate. We have found that the loss of interactions from the β-phosphate can be counterbalanced by the presence of hydrophobic groups at a pyrroline ring acting as a surrogate of the carbohydrate unit. Two of the prepared glycomimetics show inhibition at a micromolar level.

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