70831-94-6

Usage

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 
• 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 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-phthalimido-2-deoxy-α-D-glucopyranose 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 
• 85-44-9 phthalic anhydride 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 138906-41-9 4-methoxylphenzyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranoside 

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 
• 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 
• 183890-20-2 Methyl 2,4-di-O-benzyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-L-fucopyranoside 
• 183051-71-0 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-ethoxy-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester 
• 197655-22-4 C₆₈H₈₀N₄O₁₈ 
• 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 
• 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 
• 387881-23-4 (S)-2-{(R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-6-benzyloxy-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-trimethylsilanyl-ethyl ester 
• 367276-30-0 (S)-2-{(R)-2-[(2R,3S,4R,5R,6R)-2-Acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 

Relevant academic research and scientific papers

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.

CARBOHYDRATE-MODIFIED GLYCOPROTEINS AND USES THEREOF

The present invention provides immunogenic compounds which stimulate immune responses in a subject. The present invention provides compositions comprising an isolated glycoprotein antigen covalently bound at pre-existing carbohydrate residues present on the glycoprotein to a carbohydrate epitope. The present invention also provides a method to induce an immune response in a subject comprising administering the compounds of the invention. The present invention further provides methods of making the compounds of the invention and methods of using the compounds of the invention to stimulate immune responses to infectious disease agents and tumors.

Synthesis and CD structural studies of CD52 peptides and glycopeptides

The syntheses of five natural and N-terminal acetylated peptides and glycopeptides of the CD52 antigen are described. Solid phase peptide synthesis was employed in the construction of the target compounds from Fmoc-protected commercial amino acids and syn

Chemical Synthesis of CD52 Glycopeptides Containing the Acid-Labile Fucosyl Linkage

Glycopeptide 1 with the fucosylated trisaccharide, β-D-GlcNAc(1→ 4)[α-L-Fuc(1→6)]-β-D-GlcNAc, linked to the Asn of CD52 peptide was prepared by two methods, both of which used the free glycosyl Asn 12 and glycotripeptide 21 as key intermediates. Thus, after the trisaccharide was prepared and linked to Asn, the carbohydrate moiety was deprotected to give 12. From 12, 21 was constructed in homogeneous NMP solutions by elongating the peptide chain alone the N-terminus. Though the glycopeptides were easily soluble in NMP, they were barely soluble in diethyl ether, because of the free trisaccharide. Consequently, addition of diethyl ether to the reaction mixtures could precipitate the glycopeptides, and the products were conveniently isolated and purified in the solid form. The coupling of 21 with a free nonapeptide 24 in NMP afforded 1. 1 was also prepared by solid-phase synthesis, using the acid-sensitive 2-chlorotrityl resin. In this case, 21 was attached to the nonapeptide on the resin, and the resulting glycopeptide was then released with dilute acetic acid. Deprotection of the peptide under moderate acidic conditions gave 1. The acid-labile α-fucose was not affected in these syntheses.

Practical syntheses of B disaccharide and linear B type 2 trisaccharide - Non-primate epitope markers recognized by human anti-α-Gal antibodies causing hyperacute rejection of xenotransplants

Synthetic protocols are presented for the elaboration of Galα1→3GalOR and Galα1→3Galβ1→4GlcNAcOR di- and trisaccharides that use a common Gal donor/acceptor unit, and are potentially adaptable to scale-up.

Glycosylation chemistry promoted by iodine monobromide: Efficient synthesis of glycosyl bromides from thioglycosides, and O-glycosides from 'disarmed' thioglycosides and glycosyl bromides

Iodine monobromide has been found to be an efficient reagent for the conversion of both 'armed' and 'disarmed' thioglycosides (-SMe, -SPr(i), - SPh) into glycosyl bromides. This reagent is compatible with most common protecting groups, and O-glycosidic linkages. The additional potency of I- Br, compared to iodine, as an iodonium ion source also permits the glycosylation of sugar alcohols by 'disarmed' glycosyl bromides and thioglycosides.

Conversion of p-methoxyphenyl glycosides into the corresponding glycosyl chlorides and bromides, and into thiophenyl glycosides

p-Methoxyphenyl (pMP) β-D-glycopyranosides (Glc, Gal, GlcNPhth, GalNPhth, GlcNTroc, Galβ4Glc, Galα4Gal) were prepared from the corresponding 1-O-acetyl sugars in 79-90% yield, using boron trifluoride etherate as promoter. Treatment of the pMP glycosides with acyl chlorides or bromides in the presence of various Lewis acids gave the corresponding glycosyl chlorides and bromides in 81-98% yield. Treatment of the acyl-protected pMP glycosides with thiophenol and boron trifluoride etherate gave the corresponding thioglycosides in 80-100% yield and high (> 20:1) β/α selectivity. The stability of pMP glycosides was investigated against a series of reagents.

SYNTHESIS OF THE O-SPECIFIC POLYSACCHARIDE OF SHIGELLA FLEXNERI

A regular heteropolysaccharide built of tetrasaccharide repeating units is synthesised by means of regio- and stereospecific polycondensation of tritylated cyanoethylidene derivative.The polysaccharide obtained is identical with the O-antigenic polysaccharides of Shigella flexneri serotypes 3b, 3c, and variant Y.It also represents the basic chain of O-antigenic polysaccharides of all serotypes of this bacterium.