97276-95-4

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 4,6-O-Benzylidene-2-deoxy-2-N-phthalimido-b-D-glucopyranoside is used as a key intermediate in the synthesis of the O-specific polysaccharide of Shigella flexneri, a bacterium responsible for causing dysentery. The O-specific polysaccharide is an essential component of the lipopolysaccharide (LPS) present in the outer membrane of the bacterium, which plays a significant role in the pathogenesis of the disease. By synthesizing this polysaccharide, researchers can develop potential vaccines or therapeutic agents to combat Shigella infections.
Additionally, the unique structure of Methyl 4,6-O-Benzylidene-2-deoxy-2-N-phthalimido-b-D-glucopyranoside allows it to be a versatile building block for the synthesis of other complex carbohydrates and glycoconjugates, which have potential applications in various fields, such as drug discovery, diagnostics, and biomaterials. Methyl 4,6-O-Benzylidene-2-deoxy-2-N-phthalimido-b-
D-glucopyranoside's ability to form stable glycosidic linkages and its compatibility with various chemical reactions make it an attractive candidate for the development of novel pharmaceuticals and bioactive agents.

InChI:InChI=1/C22H21NO7/c1-27-22-16(23-19(25)13-9-5-6-10-14(13)20(23)26)17(24)18-15(29-22)11-28-21(30-18)12-7-3-2-4-8-12/h2-10,15-18,21-22,24H,11H2,1H3

Upstream product

• 7772-87-4 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride 
• 10028-45-2 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide 
• 76101-13-8 methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 70831-94-6 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide 
• 76101-14-9 methyl-2-desoxy-2-phthalimido-β-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 774-48-1 (diethoxymethyl)benzene 

Downstream Products

• 97242-74-5 methyl-3-O-acetyl-4,6-O-benzylidene-2-desoxy-2-phthalimido-β-D-glucopyranoside 
• 97276-96-5 methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 141542-03-2 Methyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 129114-77-8 C₄₁H₄₀F₉NO₁₈S₃ 
• 129114-78-9 C₄₈H₄₉F₆NO₁₇S₂ 
• 129090-88-6 C₄₃H₄₅F₆NO₁₆S₂ 
• 100638-50-4 methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 129090-89-7 methyl 4-O-<3-O-allyl-4,6-O-(4-methoxybenzylidene)-β-D-galactopyranosyl>-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 129090-90-0 2-{(2R,3R,4R,5S,6R)-5-[(2S,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yloxy]-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl}-isoindole-1,3-dione 
• 129090-86-4 2-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-6-allyloxymethyl-3,5-dihydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-isoindole-1,3-dione 
• 129090-87-5 2-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-isoindole-1,3-dione 
• 129090-85-3 methyl β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 129090-84-2 methyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 141542-09-8 methyl O-(2,3,4-tri-O-benzoyl-β-L-fucopyranosyl)-(1->2)-O-(3-O-benzoyl-β-D-galactopyranosyl)-(1->3)-2-deoxy-2-phthalimido-β-D-glucopyranoside 

Relevant academic research and scientific papers

Efficient Synthesis of 3,6-Dideoxy-β-D-arabino-hexopyranosyl-Terminated LacdiNac Glycan Chains of the Trichinella spiralis Parasite

The synthesis of a linear trisaccharide epitope of the Trichinella spiralis N-linked glycan, in a form amenable to glycoconjugate formation, is reported. The trisaccharide contains the synthetically challenging LacdiNAc [β-GalpNAc(1→4)-β-GlcpNAc] element,

Synthesis of methyl O-α-L-fucopyranosyl- (1 → 2)- O-β-D-galactopyranosyl- (1 → 3)- 2-acetamido- 2-deoxy-β-D-glucopyranoside, using 2,3,4-tri-O-benzoyl-α-L-fucopyranosyl bromide as the α-L-fucosylating agent

The authors cover the synthesis of trisaccharide methyl glycosides using fucosylation. Fucopyranosyl bromide was used as the fucosylating agent. The melting point, optical rotations, and NMR spectra of these glycosides are reported.

Preparation of disaccharides having a β-D-mannopyranosyl group from N-phthaloyllactosamine derivatives by double or triple SN2 substitution

Condensation of 1,2,3,4,6-penta-O-acetyl-β-D-galactopyranose with methyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside, followed by alkaline methanolysis, gave a derivative of lactosamine that has an unsubstituted β-D-galactopyranosyl group.Tr

SYNTHESIS OF DERIVATIVES OF 2-AMINO-2-DEOXY-4-O-(α- AND β-D-GALACTOPYRANOSYL)-D-GLUCOSE

Galactosylation of methyl 6-O-acetyl-3-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (5) and its trityl ether 9 with 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl bromide (8), 1-O-acetyl-2,3,4,6-tetra-O-benzoyl-β-D-galactopyranose (13), 3,4,6-tri-O-b