216877-67-7

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 216877-35-9 tert-butyldimethylsilyl 2-deoxy-2-dimethylmaleoyl-β-D-glucopyranoside 
• 315208-18-5 3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleoyl-β-D-glucopyranoside 
• 766-39-2 2,3-Dimethylmaleic anhydride 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 666728-53-6 Acetic acid (3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-(3,4-dimethyl-2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-tetrahydro-pyran-4-yl ester 
• 216876-40-3 tert-butyldimethylsilyl 3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleoyl-β-D-glucopyranoside 

Downstream Products

• 385422-23-1 tert-butyldimethylsilyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleoyl-3-O-levulinyl-β-D-glucopyranoside 
• 666728-54-7 tert-butyl(dimethyl)silyl 3-O-benzyl-4,6-O-benzylidene-2-dimethylmaleimido-2-deoxy-β-D-glucopyranoside 
• 678159-09-6 tert-butyldimethylsilyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside 
• 678159-10-9 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranose 
• 678159-11-0 1-((2R,4aR,6R,7R,8R,8aS)-8-Benzyloxy-6-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-3,4-dimethyl-pyrrole-2,5-dione 
• 678159-06-3 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl trichloroacetimidate 
• 678159-04-1 2,2,2-Trichloro-acetimidic acid (2R,4aR,6S,7R,8R,8aS)-8-benzyloxy-7-(3,4-dimethyl-2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester 
• 678159-14-3 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranose 
• 678159-12-1 tert-butyldimethylsilyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside 
• 678159-15-4 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl trichloroacetimidate 
• 678159-16-5 methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside 
• 678159-17-6 methyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside 
• 1198214-80-0 tert-butyldimethylsilyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-3-O-(2-naphthylmethyl)-β-D-glucopyranoside 
• 1198214-66-2 tert-butyldimethylsilyl 3-O-allyloxycarbonyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of a Fragment of Bacterial Cell Wall

Cell wall is indispensable for survival of bacteria. This large molecular "mesh" encases the entire cytoplasm of bacteria, and it is comprised of repeating backbone units of N-acetyl-glucosamine (NAG)-N-acetyl-muramic acid (NAM). A pentapeptide is attached to each of the lactyl units of the N-acetyl-muramic acid. The cell wall has both cross-linked and non-cross-linked components. In the present paper, we have devised a synthetic route for the preparation of a fragment of the cell wall comprised of a tetrasaccharide (NAG-NAM-NAG-NAM), along with the two appended peptides. We also report the syntheses of three glycosyl donors (compounds 5, 7, and 9) and three glycosyl acceptors (compounds 4, 6, and 8) based on the D-glucosamine structure as a building unit. The synthetic strategy that is disclosed is generally useful in construction of other natural products containing the D-glucosamine as a building block.

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.