97242-85-8

Usage

Uses

Used in Organic Synthesis:
Methyl 3-O-Benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside is used as a key intermediate in organic synthesis for the preparation of a wide range of chemical compounds. Its unique structure allows for selective functionalization and modification, enabling the synthesis of complex organic molecules with diverse applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 3-O-Benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside is used as a starting material for the synthesis of various drug candidates. Its ability to be selectively modified and functionalized makes it an ideal candidate for the development of new drugs with improved pharmacological properties, such as enhanced potency, selectivity, and reduced side effects.
Used in Chemical Research:
Methyl 3-O-Benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside is also used as a research tool in chemical research. Its unique structure and reactivity make it an interesting subject for studying various chemical reactions and mechanisms, contributing to the advancement of organic chemistry and the development of new synthetic methods.
Used in Material Science:
In the field of material science, Methyl 3-O-Benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside can be used as a building block for the synthesis of novel materials with specific properties. Its versatile structure allows for the development of materials with tailored characteristics, such as improved stability, solubility, or reactivity, which can be applied in various applications, including coatings, adhesives, and sensors.

Upstream product

• 81927-56-2 methyl 4,6-O-benzylidene-2-deoxy-2-phthalimide-β-D-glucopyranoside 
• 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 
• 119740-50-0 Methyl 2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 76101-14-9 methyl-2-desoxy-2-phthalimido-β-D-glucopyranoside 
• 155194-59-5 Methyl 3-O-benzyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside 
• 81927-58-4 methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 

Downstream Products

• 97242-86-9 methyl 3-O-benzyl-2-deoxy-2-phthalimido-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside 
• 97242-87-0 methyl 3-O-benzyl-2-deoxy-2-phthalimido-4,6-di-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside 
• 155194-60-8 Methyl 6-O-<4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl>-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 97242-88-1 methyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside 

Relevant academic research and scientific papers

Selectively Deoxyfluorinated N-Acetyllactosamine Analogues as 19F NMR Probes to Study Carbohydrate-Galectin Interactions

Galectins are widely expressed galactose-binding lectins implied, for example, in immune regulation, metastatic spreading, and pathogen recognition. N-Acetyllactosamine (Galβ1-4GlcNAc, LacNAc) and its oligomeric or glycosylated forms are natural ligands of galectins. To probe substrate specificity and binding mode of galectins, we synthesized a complete series of six mono-deoxyfluorinated analogues of LacNAc, in which each hydroxyl has been selectively replaced by fluorine while the anomeric position has been protected as methyl β-glycoside. Initial evaluation of their binding to human galectin-1 and -3 by ELISA and 19F NMR T2-filter revealed that deoxyfluorination at C3, C4′ and C6′ completely abolished binding to galectin-1 but very weak binding to galectin-3 was still detectable. Moreover, deoxyfluorination of C2′ caused an approximately 8-fold increase in the binding affinity towards galectin-1, whereas binding to galectin-3 was essentially not affected. Lipophilicity measurement revealed that deoxyfluorination at the Gal moiety affects log P very differently compared to deoxyfluorination at the GlcNAc moiety.

SYNTHESIS OF STRUCTURAL ELEMENTS OF THE CAPSULAR POLYSACCHARIDE OF STREPTOCOCCUS PNEUMONIAE TYPE 14

The synthesis is reported of methyl O-β-D-galactopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-O-4)>-O-2-acetamido-2-deoxy-β-D-glucopyranoside (13), methyl O-β-D-galactopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-O-4)>-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside (28), and O-β-D-galactopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-O-4)>-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-β-D-galactopyranosyl-(1->4)-D-glucopyranose (38), representing fragments of the capsular polysaccharide of Streptococcus pneumoniae type 14 (3)-β-D-Galp-(1->4)-β-D-Glcp-(1->6)-4)>-β-D-GlcpNAc-(1->>n). 4-O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetamidate (6) was coupled regio- and stereoselectively with HO-6 of methyl 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (4) in dichloromethane, using boron trifluoroetherate as a promoter.Coupling of 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl trichloroacetimidate (8) with HO-4 of the resulting trisaccharide derivative (9) in dichloromethane, using boron trifluoroetherate as a promoter, afforded methyl 4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-O--3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (10).Debenzylation of 10, followed by dephthaloylation, N,O-acetylation, and de-O-acetylation gave tetrasaccharide methyl glycoside 13.Disaccharide derivative 6 was also coupled with HO-6 of allyl 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (16) in dichloromethane using trimethylsilyl trifluoromethanesulfonate as a promoter.Coupling of 8 with HO-4 of the resulting trisaccharide derivative (17) in dichloromethane, using trimethylsilyl trifluoromethanesulfonate as a promoter, afforded allyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-O--3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (18).Deallylation of 18, followed by imidation gave an activated tetrasaccharide (20), which was coupled to both methyl (24) and benzyl (33) 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside in dichloromethane, using trimethylsilyl trifluoromethanesulfonate as a promoter, to give the corresponding hexasaccharide derivatives 25 and 34.Debenzylation of 25, followed by dephthaloylation, N,O-acetylation, and de-O-acetylation gave hexasaccharide methyl glycoside 28.Dephthaloylation of 34, followed by N,O-acetylation, debenzylation, re-O-acetylation and de-O-acetylation gave hexasaccharide 38.