385422-22-0

Upstream product

• 100-52-7 benzaldehyde 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 385422-21-9 3-O-acetyl-2-azido-1-O-tert-butyldimethylsilyl-2-deoxy-4,6-O-benzylidene-β-D-glucopyranoside 
• 99049-67-9 tert-Butyldimethylsilyl-2-azido-2-desoxy-β-D-glucopyranosid 
• 138923-10-1 2-azido-4,6-O-benzylidene-2-deoxyl-1-O-tert-butyldimethylsilyl-β-D-glucopyranoside 
• 99049-65-7 tert-Butyldimethylsilyl-3,4,6-tri-O-acetyl-2-azido-2-desoxy-β-D-glucopyranosid 
• 171032-74-9 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose 

Downstream Products

• 385421-83-0 tert-butyldimethylsilyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-azido-4-O-levulinyl-β-D-glucopyranoside 
• 444119-02-2 tert-butyldimethylsilyl 3-O-acetyl-2-azido-6-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-β-D-glucopyranoside 

Relevant academic research and scientific papers

One-Pot Protection Strategy of Glucosamine to Assemble Building Blocks of Chitosan and Lipid A

This investigation describes a one-pot reaction to prepare a series of building blocks for glycosylation reactions, such as 3-alcohol glucosamines, fully protected glucosamines, O-4 and O-6 alcohol glucosamines. These reactions readily produce not only gl

Modular synthesis of heparin oligosaccharides

A general, modular strategy for the first completely stereoselective synthesis of defined heparin oligosaccharides is described. Six monosaccharide building blocks (four differentially protected glucosamines, one glucuronic and one iduronic acid) were uti

Solid- and solution-phase synthesis of heparin and other glycosaminoglycans

Described is a modular, general synthetic strategy for the preparation in solution and on a solid support of heparin, heparin-like glycosaminoglycans, glycosaminoglycans and non-natural analogs of each of them. Additionally, the modular strategy provides

Linear synthesis of a protected H-type II pentasaccharide using glycosyl phosphate building blocks

A linear synthesis of a fully protected H-type II blood group determinant pentasaccharide utilizing glycosyl phosphate and glycosyl trichloroacetimidate building blocks is reported. Envisioning an automated solid-phase synthesis of blood group determinants, the utility of glycosyl phosphates in the stepwise construction of complex oligosaccharides, such as the H-type II antigen, is demonstrated. Installation of the central glucosamine building block required the screening of a variety of nitrogen protecting groups to ensure good glucosamine donor reactivity and protecting group compatibility. The challenge to differentiate C2 of the terminal galactose in the presence of other hydroxyl and amine protecting groups prompted us to introduce the 2-(azidomethyl)benzoyl group as a novel mode of protection for carbohydrate synthesis. The compatibility of this group with traditionally employed protecting groups was examined, as well as its use as a C2 stereodirecting group in glycosylations. The application of the 2-(azidomethyl)benzoyl group along with a systematic evaluation of glycosyl donors allowed for the completion of the pentasaccharide and provides a synthetic strategy that is expected to be generally amenable to the solid support synthesis of blood group determinants.