18918-50-8

Upstream product

• 93-97-0 benzoic acid anhydride 
• 13992-25-1 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 
• 41355-50-4 2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 353264-31-0 C₁₇H₂₈NO₉P 
• 604-69-3 β-D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 15354-97-9 β-1-N-benzamido-D-glucopyranose 

Relevant academic research and scientific papers

Synthesis of Glycosyl Amides Using Selenocarboxylates as Traceless Reagents for Amide Bond Formation

Carbohydrate-derived amides were successfully prepared in good yields from a broad range of substrates, including furanosyl and pyranosyl derivatives. The methodology successfully relied on the in situ generation of lithium selenocarboxylates from Se/LiEt3BH and acyl chlorides or carboxylic acids and their reaction with sugar azides. A key aspect of the present protocol is that we start from elemental selenium; isolation and handling of all reactive and sensitive selenium-containing intermediates is avoided, therefore providing the selenocarboxylate the status of a traceless reagent.

Amide-1,2,3-triazole bioisosterism: the glycogen phosphorylase case

Per-O-acetylated β-d-glucopyranosyl azide was transformed into an intermediate iminophosphorane by PMe3 which was then acylated to N-acyl-β-d-glucopyranosylamines. The same azide and substituted acetylenes gave 1-(β-d-glucopyranosyl)-4-substitu

Application of bis(diphenylphosphino)ethane (DPPE) in Staudinger-type N-glycopyranosyl amide synthesis

Bis(diphenylphosphino)ethane (DPPE) reacts with pyranosyl azides derived from d-glucose and d-glucuronic acid in the presence of acid chlorides to yield the corresponding glycosyl amides. Reaction rates are comparable to those with triphenylphosphine, how

Synthesis of a glucuronic acid and glucose conjugate library and evaluation of effects on endothelial cell growth

Compounds that alter endothelial cell growth are of interest in the development of angiogenesis modulators. A structurally diverse series of saccharide derivatives (glycosylamide conjugates) have been synthesized and evaluated for their effects on bovine

Synthesis of glucopyranosyl amides using polymer-supported reagents

2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl azide reacts efficiently with polymer-supported triphenylphosphine and various acid chlorides to yield glucopyranosyl amides with retention of the β-gluco stereochemistry.

Development of carbohydrate-based scaffolds for restricted presentation of recognition groups. Extension to divalent ligands and implications for the structure of dimerized receptors

The solution structure of glycosyl amides has been studied by using NMR. A strong preference is displayed by tertiary aromatic glycosyl amides for E-anti structures in contrast with secondary aromatic glycosyl amides where Z-anti structures predominate. The structural diversity displayed by these classes of molecules would seem to be important as the directional properties of the aromatic ring, or groups attached to the aromatic ring, would be determined by choosing to have either a secondary or tertiary amide at the anomeric center and could be considered when designing bioactive molecules with carbohydrate scaffolds. The structural analysis was also carried out for related divalent secondary and tertiary glycosyl amides and these compounds display preferences similar to that of the monovalent compounds. The constrained divalent compounds have potential for promoting formation of clusters that will have restricted structure and thus have potential for novel studies of mechanisms of action of multivalent ligands. Possible applications of such compounds would be as scaffolds for the design and synthesis of ligands that will facilitate protein - protein or other receptor - receptor interactions. The affinity of restricted divalent (or higher order) ligands, designed to bind to proteins that recognize carbohydrates which would facilitate clustering and concomitantly promote protein - protein interactions, may be significantly higher than monovalent counterparts or multivalent ligands without these properties. This may be useful as a new approach in the development of therapeutics based on carbohydrates.

An easy access to anomeric glycosyl amides and imines (Schiff bases) via transformation of glycopyranosyl trimethylphosphinimides

The preparation and application of anomeric glycosyl phosphinimides in preparative synthesis were studied. Starting from the appropriate glycosyl azides and trialkyl or triaryl phosphines, the corresponding phosphinimides were obtained by modified Staudin