99745-44-5

Upstream product

• 96622-49-0 4,6-Benzyliden-N-benzoyl-methyl-β-D-allosaminid 
• 7334-25-0 Methyl-2-benzoylamino-2-desoxy-β-D-glucopyranosid 
• 81927-56-2 methyl 4,6-O-benzylidene-2-deoxy-2-phthalimide-β-D-glucopyranoside 
• 76101-14-9 methyl-2-desoxy-2-phthalimido-β-D-glucopyranoside 
• 3055-46-7 methyl N-acetyl-D-glucosamine 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 99679-76-2 Methyl-2-benzoylamino-3,4,6-tri-O-benzoyl-2-desoxy-β-D-glucopyranosid 
• 99745-43-4 Methyl-2-benzoylamino-4,6-O-benzyliden-2-desoxy-β-D-glucopyranosid 
• 87038-18-4 methyl 2-acetylamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 

Downstream Products

• 96622-67-2 Methyl-4,6-O-benzyliden-2-desoxy-2-(2,4-dinitroanilino)-β-D-allopyranosid 
• 148546-35-4 Methyl 4,6-O-benzylidene-2-deoxy-2-trifluoroacetamido-β-D-glucopyranoside 
• 274260-02-5 methyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 1185733-95-2 methyl 4,6-O-benzylidene-2,3-dideoxy-2,3-imino-N-(trichloroethoxysulfonyl)-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.

D-Glucosamine as a novel chiral auxiliary for the stereoselective synthesis of P-stereogenic phosphine oxides

D-Glucosamine was successfully employed as a chiral auxiliary for the enantioselective synthesis of phosphine oxides. The influence of the anomeric position was also investigated and revealed the excellent ability of the α-anomer to perform this transform

Synthesis of Diverse N-Substituted Muramyl Dipeptide Derivatives and Their Use in a Study of Human NOD2 Stimulation Activity

A flexible synthetic strategy toward the preparation of diverse N-substituted muramyl dipeptides (N-substituted MDPs) from different protected monosaccharides is described. The synthetic MDPs include N-acetyl MDP and N-glycolyl MDP, known NOD2 ligands, and this methodology allows for structural variation at six positions, including the muramic acid, peptide, and N-substituted moieties. The capacity of these molecules to activate human NOD2 in the innate immune response was also investigated. It was found that addition of the methyl group at the C1 position of N-glycolyl MDP significantly enhanced the NOD2 stimulating activity.

Oligo-Aminosaccharide compound

An oligo-aminosaccharide compound formed by binding 3 to 6 saccharides, such as 2,6-diamino-2,6-dideoxy-α-(1→4)-D-glucopyranose oligomers, or a salt thereof, which has high affinity to a double-stranded nucleic acid.

Accessible sugars as asymmetric olefin epoxidation organocatalysts: Glucosaminide ketones in the synthesis of terminal epoxides

A systematically varied series of conformationally restricted ketones, readily prepared from N-acetyl-d-glucosamine, were tested against representative olefins as asymmetric epoxidation catalysts showing useful selectivities against terminal olefins and, in particular, typically difficult 2,2-disubstituted terminal olefins.

Carbohydrate-derived aminoalcohol ligands for asymmetric Reformatsky reactions

Members of a family of functionally and stereochemically diverse d-glucosamine-derived tertiary aminoalcohol ligands have been used to promote the asymmetric Reformatsky reaction. The β-hydroxyester product tert-butyl 3-phenyl-3-hydroxy-propanoate was obt

Precise structure activity relationships in asymmetric catalysis using carbohydrate scaffolds to allow ready fine tuning: dialkylzinc-aldehyde additions.

The ready construction of 24 stereochemically and functionally diverse carbohydrate ligand structures from a core D-glucosamine scaffold has allowed the evaluation of broad ranging structure activity relationships in ligand accelerated zincate additions t

Selectively protected disaccharide building blocks for modular synthesis of heparin fragments

A modular approach for the synthesis of heparin fragments is described. Levulinoyl esters were employed to protect those hydroxy groups intended to be sulfated in the final product, while acetyl esters and benzyl ethers were used as the permanent protecting groups. A highly efficient chemoenzymatic reaction sequence was used for the deprotection of an O-sulfated fragment, while the final stage of the synthesis entailed a selective oxidation of a primary alcohol of a glucoside with TEMPO/NaOCl to give a glucuronic acid moiety. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

The synthesis of chemically modified disaccharide derivatives of the Shigella flexneri Y polysaccharide antigen

Disaccharide analogs related to the 2-acetamido-2-deoxy-3-O-(α-L-rhamnopyranosyl)-β-D-glucopyranose element of the Shigella flexneri Y polysaccharide antigen have been synthesized and used to map the binding site of murine monoclonal antibodies GC-4 and S

Enolates of Carbohydrates, 4. - Axial C-Alkylation in α-Position of α-Amino-α-deoxy-ketoses

Products of type 2a-c, 6, 10a, b, and 14a, b which are alkylated in α-position of the keto function are yielded by reaction of the α-amino-α-deoxy-uloses 1a-c, 5, 9a, and 13a, b with LDA, CH3I, HMPA in THF (method A) or KOtBu, CH3I in DMF (method B) in a