1000403-62-2

Upstream product

• 676487-75-5 methyl 3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 898547-26-7 1-((2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-3,4-dimethyl-pyrrole-2,5-dione 

Downstream Products

• 1000403-60-0 methyl 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 
• 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 
• 678159-03-0 methyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside 
• 678159-08-5 methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranose 

Relevant academic research and scientific papers

Differential O-3/O-4 regioselectivity in the glycosylation of α and β anomers of 6-O-substituted N-dimethylmaleoyl-protected d-glucosamine acceptors

An assessment of the relative O-3/O-4 reactivities of both methyl α- and β-d-glycosides of N-dimethylmaleoyl (DMM) d-glucosamine acceptors protected at O-6 with benzoyl (Bz), benzyl (Bn), and tert-butyldiphenylsilyl (TBDPS) groups is presented using per-O

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.