195976-07-9

Usage

Uses

Used in Organic Synthesis:
O-(2-Azido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranosyl)-N-Fmoc-L-threonine tert-Butyl Ester is used as a versatile intermediate for the synthesis of complex organic molecules. Its azido group can be utilized in click chemistry reactions, allowing for the efficient and selective formation of new chemical bonds, which is crucial for the development of novel compounds with specific properties.
Used in Pharmaceutical Chemistry:
In the pharmaceutical industry, O-(2-Azido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranosyl)-N-Fmoc-L-threonine tert-Butyl Ester is used as a building block for the development of new drugs. Its unique structure and functional groups can be employed to create bioactive molecules with potential therapeutic applications. O-(2-Azido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranosyl)-N-Fmoc-L-threonine tert-Butyl Ester's reactivity and the presence of protecting groups enable the synthesis of diverse drug candidates with tailored properties.
Used in Drug Delivery Systems:
O-(2-Azido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranosyl)-N-Fmoc-L-threonine tert-Butyl Ester can be used as a component in the design of drug delivery systems. Its functional groups and reactivity can be exploited to create targeted drug carriers or to improve the solubility, stability, and bioavailability of therapeutic agents. This application can enhance the efficacy and safety of drug treatments, particularly for challenging drug targets.
Used in Glycobiology Research:
In the field of glycobiology, O-(2-Azido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranosyl)-N-Fmoc-L-threonine tert-Butyl Ester is used as a research tool to study the role of glycans in biological processes. Its galactopyranosyl moiety can be employed to investigate glycan-mediated interactions, such as cell adhesion, immune responses, and cell signaling, providing insights into the molecular mechanisms underlying various diseases and conditions.

InChI:InChI=1/C36H40N4O9/c1-20(46-34-29(39-40-37)30(41)31-27(47-34)19-44-33(48-31)21-12-6-5-7-13-21)28(32(42)49-36(2,3)4)38-35(43)45-18-26-24-16-10-8-14-22(24)23-15-9-11-17-25(23)26/h5-17,20,26-31,33-34,41H,18-19H2,1-4H3,(H,38,43)/t20-,27+,28+,29+,30-,31+,33?,34+/m1/s1

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 195976-26-2 (2S,3R)-3-((2S,3R,4R,5R,6R)-3-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid tert-butyl ester 
• 120791-77-7 N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-azido-2-desoxy-α-D-galactopyranosyl)-1-threonine tert-butyl ester 
• 120173-56-0 N^α-(9-fluorenylmethoxycarbony)-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-L-threonine tert-butyl ester 

Downstream Products

• 195976-15-9 N^α-(fluoren-9-ylmethoxycarbonyl)-O-[O-[3',4',6'-tri-O-benzoyl-2'-deoxy-2'-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-(1'->3)]-2-azido-2-deoxy-α-D-galactopyranosyl]-L-threonine tert-butyl ester 
• 195976-08-0 N-[(9H-fluoren-9-yl)-methoxycarbonyl]-O-[O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-galactopyranosyl)-(1''-3)-(2-azido-4O,6O-benzylidene-2-deoxy-α-D-galactopyranosyl)]-L-threonine tert-butyl ester 

Relevant academic research and scientific papers

Revealing Functional Significance of Interleukin-2 Glycoproteoforms Enabled by Expressed Serine Ligation

Naturally occurring interleukin-2 (IL-2) is a pleiotropic glycoprotein that regulates immune responses by controlling the differentiation and homeostasis of T cells. Non-glycosylated IL-2 has been used in clinical settings for three decades. However, the function of the O-glycan of native IL-2 remains elusive. Herein, to stress this issue, we report a highly efficient semi-synthesis of homogeneous glycosylated IL-2 with various glycoproteoforms on a multi-milligram scale. The glycopeptide fragment was prepared by chemical synthesis and then merged with recombinant fragment via a serine ligation to generate the desired glycoprotein in a single operation. Biological evaluation of the homogenous glycoprotein library reveals that the activity of IL-2 in activating individual T cell subset is glycan dependent, thus highlighting the possibility of further improving current clinical medicine.

Stereoselective synthesis of sialylated tumor-associated glycosylamino acids

Suitably protected sialyl TN and 2,6-sialyl T tumor-associated carbohydrate antigen-derived amino acids have been prepared stereoselectively using an oxazolidinone-derived sialoside donor. These glycosylamino acids can be employed directly in t

Synthesis of glycopeptide sequences of repeating units of the mucins MUC 2 and MUC 3 containing oligosaccharide side-chains with core 1, core 2, core 3, core 4 and core 6 structure

An efficient synthesis of glycosylamino acid building blocks containing core 1, core 2, core 3, core 4 or core 6 mucin core oligosaccharide structures linked O-glycosidically to threonine has been developed. These building blocks 6, 10, 16, 24 and 30 can be used directly for coupling reactions in a glycopeptide synthesis. In a multiple-column solid-phase synthesis, they have been used to prepare different series of glycopeptides. Decapeptide sequences have been synthesized from repeating units of the mucins MUC 2 and MUC 3 in which different threonine residues are each systematically glycosylated with an oligosaccharide of core 1, core 2, core 3, core 4 or core 6 structure. Glycopeptides are substrates for the study of the biosynthesis of the saccharide side-chains of mucins.