102816-24-0

Usage

Uses

Used in Organic Synthesis:
3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl azide is used as a building block in organic synthesis for the creation of complex organic molecules, leveraging its unique functional groups to form diverse chemical structures.
Used in Chemical Biology Research:
In the field of chemical biology, 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl azide serves as a valuable tool for studying the roles of glycans and glycosylation in biological processes, given its ability to be selectively modified and incorporated into biomolecules.
Used in Drug Development:
3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl azide is utilized in the development of new pharmaceuticals, particularly in the design of glycoconjugate drugs, where its reactivity and stability are crucial for creating effective therapeutic agents.
Used in Materials Science:
3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl azide is also applied in materials science for the development of new materials with specific properties, such as biocompatibility or targeted drug delivery capabilities, by incorporating its unique chemical structure into the material's composition.
Used in Glycosylation and Glycan Biology Studies:
3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl azide is used as a research compound in glycosylation and glycan biology to explore the intricate roles of carbohydrates in cell recognition, signaling, and disease processes, taking advantage of its ability to be selectively modified for specific interactions.

Upstream product

• 85-44-9 phthalic anhydride 

Downstream Products

• 1361485-97-3 1-(2′-deoxy-2′-phthalimido-3′,4′,6′-tri-O-acetyl-β-D-glucopyranosyl)-4-phenyl-1,2,3-triazole 
• 191037-58-8 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 
• 191037-60-2 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 
• 182923-92-8 3-O-benzyl-2-deoxy-6-O-(p-methoxyphenyl)-2-phthalimido-β-D-glucopyranosyl azide 
• 1404438-26-1 C₂₂H₁₉F₃N₄O₈S 
• 218961-16-1 O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-(1->6)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 
• 218961-14-9 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 
• 449177-47-3 3-O-benzyl-4,6-O-benzylidene-2-p-nitrobenzoyl-β-D-glucopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-p-methoxybenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 
• 449177-43-9 acetic acid 3-acetoxy-6-[6-azido-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester 
• 449177-45-1 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-6-O-p-methoxybenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 
• 449177-35-9 6-O-p-methoxybenzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 
• 449177-33-7 2-[(2R,4aR,6R,7R,8R,8aS)-6-Azido-8-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione 
• 543719-74-0 O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1*4)-6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 
• 543719-73-9 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 

Relevant academic research and scientific papers

Synthesis of novel N-glycoside derivatives via CuSCN-catalyzed reactions and their SGLT2 inhibition activities

A convenient approach to the synthesis of novel triazole-N-glycoside derivatives was developed via CuSCN-catalyzed click reaction and Ullmann-type coupling reaction for the first time. The SGLT2 inhibitory activities of these synthetic N-glycosides were evaluated, and some compounds showed moderate SGLT2 inhibition activities at 100 nM. The results could benefit the discovery of new SGLT2 inhibitors for the treatment of diabetes.

Structure activity relationships of N-linked and diglycosylated glucosamine-based antitumor glycerolipids

1-O-Hexadecyl-2-O-methyl-3-O-(2′-amino-2′-deoxy-β-D- glucopyranosyl)-snglycerol (1) was previously reported to show potent in vitro antitumor activity on a range of cancer cell lines derived from breast, pancreas and prostate cancer. This compound was not toxic to mice and was inactive against breast tumor xenografts in mice. This inactivity was attributed to hydrolysis of the glycosidic linkage by glycosidases. Here three N-linked (glycosylamide) analogs 2-4, one triazole-linked analog 5 of 1 as well as two diglycosylated analogs 6 and 7 with different stereochemistry at the C2-position of the glycerol moiety were synthesized and their antitumor activity against breast (JIMT-1, BT-474, MDA-MB-231), pancreas (MiaPaCa2) and prostrate (DU145, PC3) cancer cell lines was determined. The diglycosylated analogs 1-O-hexadecyl-2(R)-, 3-O-di-(2′-amino-2′-deoxy- β-D- glucopyranosyl)-sn-glycerol (7) and the 1:1 diastereomeric mixture of 1-O-hexadecyl- 2(R/S), 3-O-di-(2′-amino-2′-deoxy-β-D- glucopyranosyl)-sn-glycerol (6) showed the most potent cytotoxic activity at CC50 values of 17.5 μM against PC3 cell lines. The replacement of the O-glycosidic linkage by a glycosylamide or a glycosyltriazole linkage showed little or no activity at highest concentration tested (30 μM), whereas the replacement of the glycerol moiety by triazole resulted in CC50 values in the range of 20 to 30 μM. In conclusion, the replacement of the O-glycosidic linkage by an N-glycosidic linkage or triazole-linkage resulted in about a two to three fold loss in activity, whereas the replacement of the methoxy group on the glycerol backbone by a second glucosamine moiety did not improve the activity. The stereochemistry at the C2-position of the glycero backbone has minimal effect on the anticancer activities of these diglycosylated analogs.