220688-23-3

Upstream product

• 183875-35-6 phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-azido-1-thiol-α-D-glucopyranoside 
• 108-98-5 thiophenol 
• 171032-74-9 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose 
• 183875-02-7 phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 277756-85-1 phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-α-D-glucopyranoside 

Relevant academic research and scientific papers

Conformational Lock of Glycosyl Donors Using Cyclic Carbamates

Axial rich glycosyl donors often display superior reactivity and stereoselectivity in glycosylations. In this study, a glucosamine glycosyl donor, locked in a 1C4 conformation by a six-membered carbamate ring, i.e. an oxazinone, is synthesized and studied. The 2N,4O carbamate is synthesized in one step from the corresponding azide. The glycosylation properties were studied by glycosylating different alcohols. Derivatives of the glycosyl donor were synthesized by introducing Ac, Troc, Ts, and Ms groups on the oxazinone nitrogen. The ring opening to give the glycoside in the 4C1 conformation was found to proceed smoothly using Zemplén conditions.

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.