277756-87-3

Upstream product

• 100-39-0 benzyl bromide 
• 166516-67-2 phenyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 277756-86-2 phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside 
• 1394857-30-7 phenyl 4,6-O-benzylidene-1-thio-β-D-glucosaminopyranoside 
• 56644-75-8 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroacetamido)-β-D-glucopyranose 
• 169557-87-3 phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-trichloroacetamido-β-D-glucopyranoside 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 371123-22-7 phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside 
• 108-98-5 thiophenol 
• 277756-84-0 phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside 

Downstream Products

• 277756-89-5 phenyl 2-azido-3,6-di-O-benzyl-4-O-(tert-butyldimethylsilyl)-2-deoxy-1-thio-β-D-glucopyranoside 
• 1400562-67-5 2-azido-3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-α-D-galactopyranosyl fluoride 
• 1400562-68-6 2-azido-3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-β-D-galactopyranosyl fluoride 
• 1400562-27-7 phenyl 2-azido-3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 1394857-34-1 phenyl 2-azido-2-deoxy-3,6-di-O-benzyl-4-O-trichloroacetyl-1-thio-β-D-glucopyranoside 
• 1394857-57-8 methyl [phenyl 4-O-(2-azido-3,6-O-dibenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-β-L-ido-pyranoside]uronate 
• 1394857-53-4 methyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-trichloroacetyl-α-D-glucopyranosyl-(1→4)-(phenyl-2-O-benzoyl-3-O-benzyl-1-thio-β-L-idopyranoside)uronate 
• 1394857-52-3 methyl [phenyl 4-O-(2-azido-3,6-O-dibenzyl-2-deoxy-4-O-trichloroacetyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-L-idopyranoside]uronate 
• 1394857-51-2 methyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1→4)-(phenyl 3-O-benzyl-2-O-benzoyl-1-thio-β-L-idopyranoside)uronate 
• 915154-77-7 C₄₆H₅₁N₃O₁₄ 
• 1394857-47-6 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate 
• 1253183-67-3 phenyl [tert-butyl (3,4-di-O-benzyl-2-O-benzoyl-β-D-glucopyranosyl)uronate]-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside) 
• 154920-28-2 2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate 

Relevant academic research and scientific papers

Mechanistic Investigation of 1,2-Diol Dehydration of Paromamine Catalyzed by the Radical S-Adenosyl- l -methionine Enzyme AprD4

AprD4 is a radical S-adenosyl-l-methionine (SAM) enzyme catalyzing C3′-deoxygenation of paromamine to form 4′-oxo-lividamine. It is the only 1,2-diol dehydratase in the radical SAM enzyme superfamily that has been identified and characterized in vitro. The AprD4 catalyzed 1,2-diol dehydration is a key step in the biosynthesis of several C3′-deoxy-aminoglycosides. While the regiochemistry of the hydrogen atom abstraction catalyzed by AprD4 has been established, the mechanism of the subsequent chemical transformation remains not fully understood. To investigate the mechanism, several substrate analogues were synthesized and their fates upon incubation with AprD4 were analyzed. The results support a mechanism involving formation of a ketyl radical intermediate followed by direct elimination of the C3′-hydroxyl group rather than that of a gem-diol intermediate generated via 1,2-migration of the C3′-hydroxyl group to C4′. The stereochemistry of hydrogen atom incorporation after radical-mediated dehydration was also established.

HClO4-silica-catalysed regioselective opening of benzylidene acetals and its application towards regioselective HO-4 glycosylation of benzylidene acetals in one-pot

Here we report a high-yielding method for the regioselective reductive ring opening of 4,6-O-benzylidene acetals of hexapyranosides using inexpensive and robust HClO4-SiO2 as the acidic catalyst and triethylsilane as the hydride dono

Synthesis and scalable conversion of L-iduronamides to heparin-related Di- and tetrasaccharides

A diastereomerically pure cyanohydrin, preparable on kilogram scale, is efficiently converted in one step into a novel L-iduronamide. A new regioselective acylation of this iduronamide and a new mild amide hydrolysis method mediated by amyl nitrite enable

Single-step multisyntheses of glycosyl acceptors: Benzylation of n-1 hydroxyl groups of phenylthio glycosides of xylose, mannose, glucose, galactose, 2-azido-2-deoxy-glucose, and 2-azido-2-deoxy-galactose

An array of synthons is required to access an oligosaccharide library; however, multistep and thus time-consuming synthesis is inevitable. To rapidly access such synthetic units, multiple benzylation reactions of monosaccharides under phase-transfer condi

Efficient routes to glucosamine-myo-inositol derivatives, key building blocks in the synthesis of glycosylphosphatidylinositol anchor substances

Short synthetic routes to protected derivatives of 2-amino-2-deoxy-α-D-glucopyranosyl-(1→6)-D-myo-inositol are described. Various 2-azido-2-deoxy-glucosyl donors were synthesized, starting from D-glucal or glucosamine hydrochloride. Derivatives of 1,2- and 2,3- D-myo-inositol-camphanylidene acetals were prepared to function as glycosyl acceptors. The subsequent glycosylations produced useful building blocks for the synthesis of GPI-anchor substances.

Attempted synthesis of type-A inositolphosphoglycan mediators - Synthesis of a pseudohexasaccharide precursor

A block synthesis approach to the inositol-containing pseudohexasaccharide 1 is presented. The myo-inositol building block 6 has been prepared using a key regioselective acylation through a boron-tin exchange reaction and the 2-azido-2-deoxy glycosyl donors 15 and 17 have been synthesized from D-glucosamine using a diazo transfer reaction. The anomeric position of the mono- and disaccharide building blocks has been temporarily protected as phenyl thioglycoside and this function was then converted into the different leaving groups to perform the glycosylation reactions. Both trichloroacetimidates and fluorides have been used as glycosyl donors for the construction of the different glycosidic linkages. The protected pseudohexasaccharides 44, 48-50, which are precursors of pseudohexasaccharide 1, have been efficiently prepared and fully characterized. Pseudohexasaccharide 1 contains the fundamental structural features which have been proposed for type A inositolphosphoglycans, which may be involved in the insulin-signaling process.