40299-08-9

Upstream product

• 384346-98-9 methyl 3-O-tert-butyldimethylsilyl-4,6-O-p-methoxybenzylidene-2-deoxy-2-trifluoroacetamido-β-D-glucopyranoside 
• 28719-32-6 methyl 3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-β-D-glucopyranoside 
• 7139-63-1 1,3,4,6-tetra-O-acetyl-2-(trifluoroacetamido)-2-deoxy-β-D-glucopyranoside 
• 187880-20-2 2,6-anhydro-5-deoxy-1,3-O-(4-methoxybenzylidene)-D-arabino-hex-5-enitol 
• 273749-60-3 phenyl 4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside 
• 340320-92-5 tert-butyl(((2R,4aR,8R,8aR)-2-(4-methoxyphenyl)-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)dimethylsilane 

Downstream Products

• 660438-46-0 2-fluoro-N-(4-methoxy-benzyl)-N-(6-methoxy-2,2-dimethyl-8-triethylsilanyloxy-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-5-nitro-benzamide 
• 660438-47-1 2-fluoro-N-(6-methoxy-2,2-dimethyl-8-triethylsilanyloxy-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-5-nitro-N-pyridin-2-ylmethyl-benzamide 
• 660438-45-9 N-benzyl-2-fluoro-N-(6-methoxy-2,2-dimethyl-8-triethylsilanyloxy-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-5-nitro-benzamide 
• 660438-35-7 (4aR,6R,6aR,13aR,13bS)-7,13-Dibenzyl-6-methoxy-2,2-dimethyl-10-nitro-4a,6a,7,13,13a,13b-hexahydro-4H,6H-1,3,5-trioxa-7,13-diaza-benzo[5,6]cyclohepta[1,2-a]naphthalen-8-one 
• 660438-43-7 (4-Methoxy-benzyl)-((4aR,6R,7R,8R,8aR)-6-methoxy-2,2-dimethyl-8-triethylsilanyloxy-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-amine 

Relevant academic research and scientific papers

Stereoselective synthesis of [13C]methyl 2-[15N]amino-2-deoxy-beta-D-glucopyranoside derivatives.

Efficient syntheses of three [13C]methyl 2-[15N]amino-2-deoxy-beta-D-glucopyranoside derivatives are described. Amination of the D-glucal with (saltmen)Mn(15N) proceeded with 11:1 stereoselectivity favoring the gluco configuration; subsequent methylation of the [15N]lactol using [13C]iodomethane and silver(I) oxide afforded the doubly labeled beta glucoside in high yield. This compound served as the common precursor for three [13C]methyl 2-[15N]aminoglucosides: (2-[15N]trifluoroacetyl-), (2-[15N]acetyl-), and (2-[15N]azido-). Selected heteronuclear coupling constants are reported.

Probing synergy between two catalytic strategies in the glycoside hydrolase O-GlcNAcase using multiple linear free energy relationships

Human O-GlcNAcase plays an important role in regulating the post-translational modification of serine and threonine residues with β-O-linked N-acetylglucosamine monosaccharide unit (O-GlcNAc). The mechanism of O-GlcNAcase involves nucleophilic participation of the 2-acetamido group of the substrate to displace a glycosidically linked leaving group. The tolerance of this enzyme for variation in substrate structure has enabled us to characterize O-GlcNAcase transition states using several series of substrates to generate multiple simultaneous free-energy relationships. Patterns revealing changes in mechanism, transition state, and rate-determining step upon concomitant variation of both nucleophilic strength and leaving group abilities are observed. The observed changes in mechanism reflect the roles played by the enzymic general acid and the catalytic nucleophile. Significantly, these results illustrate how the enzyme synergistically harnesses both modes of catalysis; a feature that eludes many small molecule models of catalysis. These studies also suggest the kinetic significance of an oxocarbenium ion intermediate in the O-GlcNAcase-catalyzed hydrolysis of glucosaminides, probing the limits of what may be learned using nonatomistic investigations of enzymic transition-state structure and offering general insights into how the superfamily of retaining glycoside hydrolases act as efficient catalysts.

A chemoenzymatic approach to glycopeptide antibiotics

Many biologically active natural products are constrained by macrocyclization and modified with carbohydrates. These two types of modifications are essential for their biological activities. Here we report a chemoenzymatic approach to make carbohydrate-mo