459170-35-5

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 732246-93-4 (tert-butyl)dimethylsilyl 2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 459170-34-4 (tert-butyl)dimethylsilyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 72858-55-0 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 

Downstream Products

• 514792-62-2 3,6-di-O-benzyl-1-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 1203588-94-6 2-acetamido-4-O-(2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranose 
• 1203588-93-5 tert-butyldimethylsilyl 2-acetamido-4-O-(2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 1203588-92-4 tert-butyldimethylsilyl 2-acetamido-4-O-(4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 1203582-46-0 tert-butyldimethylsilyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-deoxy-3,6-di-O-benzyl-2-phthalimido-β-D-glucopyranoside 
• 1203588-91-3 tert-butyldimethylsilyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 459170-38-8 tert-butyldimethylsilyl 4-O-benzoyl-3-O-[(benzyloxy)methyl]-2,6-dideoxy-6-bromo-2-phthalimido-β-D-glucopyranoside 
• 459170-44-6 tert-butyldimethylsilyl 4-O-acetyl-3-O-[(benzyloxy)methyl]-2,6-dideoxy-6-phenylseleno-2-trifluoroacetamido-β-D-glucopyranoside 
• 459170-64-0 N-[(2S,3R,4R,5S,6S)-4-Benzyloxymethoxy-2-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-6-phenylselanylmethyl-tetrahydro-pyran-3-yl]-2,2,2-trifluoro-acetamide 
• 459170-42-4 tert-butyldimethylsilyl 3-O-[(benzyloxy)methyl]-2,6-dideoxy-6-phenylseleno-2-amino-β-D-glucopyranoside 

Relevant academic research and scientific papers

Selection of protecting groups and synthesis of a β-1,4-GlcNAc-β- 1,4-GlcN unit

The synthesis of the disaccharide tert-butyldimethylsilyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-d-glucopyranosyl)-3, 6-di-O-benzyl-2-deoxy-2-phthalimido-β-d-glucopyranoside, designed as a repeating unit appearing in oligo- and polysaccharides, whi

Synthesis of 5-fluoro N-acetylglucosamine glycosides and pyrophosphates via epoxide fluoridolysis: Versatile reagents for the study of glycoconjugate biochemistry

Numerous carbohydrate-processing enzymes facilitate catalysis via stabilization of positive charges on or near the C-1, C-4, C-5, or C-6 positions. Substrate analogues differing only in the substitution of a fluorine for the axial C-5 hydrogen would possess reduced electron density at these positions and could be useful mechanistic probes of these enzymes. Introduction of this 5-fluoro substituent after radical halogenation was problematic because of the incompatibility of many protecting groups to the radical halogenation and the instability of the subsequent 5-fluoro hexosamines. Thus, to allow easy access to a wide variety of 5-fluoro glycosides and glycosyl phosphates, a versatile method for the introduction of the 5-fluoro group has been developed, the key step being the fluoridolysis of C-5, 6 epoxides. By use of this method, two fluorinated carbohydrates, uridine 5′-diphospho-5-fluoro-N-acetylglucosamine and octyl 5-fluoro-N-acetylglucosamine, have been synthesized. Initial biochemical investigations of these compounds show that 5-fluoro analogues are useful probes of transition-state charge development in several enzyme-catalyzed reactions.