70428-25-0

Upstream product

• 2280-44-6 D-Glucose 
• 100-46-9 benzylamine 
• 59-23-4 D-Galactose 
• 622-79-7 benzyl azide 
• 13992-25-1 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 100-52-7 benzaldehyde 
• 492-62-6 alpha-D-glucopyranose 
• 50-99-7 D-glucose 

Downstream Products

• 99782-83-9 N-acetyl-2,3,4,6-tetra-O-acetyl-N-benzyl-β-D-glucopyranosylamine 
• 50-99-7 D-glucose 
• 100-46-9 benzylamine 
• 74015-32-0 1-Benzyl-3-(2-chloro-ethyl)-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-urea 
• 74015-33-1 C₁₆H₂₂ClN₃O₇ 

Relevant academic research and scientific papers

Study of the isomeric Maillard degradants, glycosylamine and Amadori rearrangement products, and their differentiation via MS2 fingerprinting from collision-induced decomposition of protonated ions

Rationale: The focus of this work was to study glycosylamine and Amadori rearrangement products (ARPs), the two major degradants in the Maillard reactions of pharmaceutical interest, and utilize their MS2 fingerprints by liquid chromatography/high-resolution tandem mass spectrometry (LC/HRMS2) to quickly distinguish the two isomeric degradants. These two types of degradants are frequently encountered in the compatibility and stability studies of drug products containing primary or secondary amine active pharmaceutical ingredients (APIs), which are formulated with excipients consisting of reducing sugar functionalities. Methods: Vortioxetine was employed as the primary model compound to react with lactose to obtain the glycosylamine and ARP degradants of the Maillard reaction, and their MS2 spectra (MS2 fingerprints) were obtained by LC/MS2. Subsequently, the two degradants were isolated via preparative HPLC and their structures were confirmed by one- and two-dimensional (1D and 2D) nuclear magnetic resonance (NMR) determination. Results: The MS2 fingerprints of the two degradants display significantly different profiles, despite the fact that many common fragments are observed. Specifically, protonated glycosylamine shows a prominent characteristic fragment of [Mvort + C2H3O]+ at m/z 341 (Mvort is the vortioxetine core), while protonated ARP shows a prominent characteristic fragment of [Mvort + CH]+ at m/z 311. Further study of the Maillard reactions between several other structurally diverse primary/secondary amines and lactose produced similar patterns. Conclusions: The study suggests that the characteristic MS2 fragment peaks and their ratios may be used to differentiate the glycosylamine and ARP degradants, the two isomeric degradants of the Maillard reaction, which are commonly encountered in finished dosage forms of pharmaceutical products containing primary and secondary amine APIs.

Direct synthesis of β-N-glycosides by the reductive glycosylation of azides with protected and native carbohydrate donors

A simple and straightforward method for the stereocontrolled synthesis of β-linked N-glycosides uses alkyl and aryl azides as the nitrogen source. The N-glycosides are formed in high yields and with high βselectivities (typically >70 % yield, >15:1 β:α selectivity). This approach is also amenable to the synthesis of N-glycosylated amino acids and peptides (see example, Fmoc=9-fluorenylmethoxycarbonyl). Copyright

Green glycosylation using ionic liquid to prepare alkyl glycosides for studying carbohydrate-protein interactions by SPR

Several simple glycosides of d-glucose (Glc) and N-acetyl-d-galactosamine (GalNAc) were prepared in a single step glycosylation reaction using unprotected and unactivated sugar donors. The resulting GalNAc glycoside, containing a bifunctional linker, was used to immobilize this glycoconjugate to a self assembled monolayer on a gold biosensor chip. Surface plasmon resonance (SPR) experiments demonstrated that this immobilized glycoconjugate bound to GalNAc specific lectin, Viscum album agglutinin.

Synthesis and fungicidal activity of alkaloid-containing carbohydrates

N-Glycosylamines, triethylammonium salt of xylosyl- and glucosylbenzyldithiocarbamates, and their derivatives containing fragments of alkaloids were synthesized; some of these substances exhibit fungicidal activity. Pleiades Publishing, Inc., 2006.

N-glycosylated carboxamide derivatives as growth-promoters in livestock feeding

Growth of animals is promoted by inclusion in their feed of compounds of the formula STR1 in which Z is a glycosyl radical bonded via the anomeric carbon atom, R1 is hydrogen or an optionally substituted hydrocarbon radical having up to 30 Carb

N-glycosylated carboxylic acid derivatives as agents for combating rheumatic diseases

A method of combating rheumatic diseases which comprises administering to a patient afflicted therewith an amount effective to combat such disease of a compound of the formula STR1 in which Z is a glycosyl radical bonded via the anomeric carbon atom, Rsu

N-glycosylated carboxamide derivatives and their use for influencing the body's inherent defences

The invention relates to N-glycosylated carboxamide derivatives of Formula I which are useful for influencing the body's inherent defenses, e.g. for increasing immune system antibodies. Also included in the invention are compositions containing said N-gly