310870-34-9

Upstream product

• 108-98-5 thiophenol 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 202462-37-1 phenyl 2-azido-2-deoxy-1-thio-α/β-D-glucopyranoside 
• 183875-22-1 phenyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-α/β-D-glucopyranoside 
• 171032-74-9 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose 

Downstream Products

• 439683-93-9 (2R,4aR,7R,8R,8aS)-7-Azido-8-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 367518-26-1 trichloroacetoimidoyl 4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α/β-D-glucopyranoside 
• 310870-32-7 Acetic acid (2R,3S,4R,5R)-5-azido-4-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester 
• 439683-95-1 phenyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-D-glucopyranoside 
• 310870-37-2 O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate 
• 918868-69-6 toluene-4-sulfonic acid 5-azido-4-benzyloxy-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester 
• 918868-75-4 acetic acid 5-azido-2-azidomethyl-4-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester 
• 918868-71-0 5-azido-2-azidomethyl-4-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-3-ol 
• 918868-67-4 5-azido-4-benzyloxy-2-hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol 

Relevant academic research and scientific papers

Synthesis of aminoglycoside derivatives on a Cbz-type heavy fluorous tag

Four aminoglycoside derivatives containing a 2,6-diamino-2,6-dideoxy-d-glucopyranose disaccharide structure were successfully prepared by using a Cbz-type heavy fluorous tag in a fluorous synthesis. A Cbz-type heavy fluorous tag was prepared using the hex

Inositolphosphoglycan mediators structurally related to glycosyl phosphatidylinositol anchors: Synthesis, structure and biological activity

The preparation of the pseudopentasaccharide 1a, an inositolphosphoglycan (IPG) that contains the conserved linear structure of glycosyl phosphatidylinositol anchors (GPI anchors), was carried out by using a highly convergent 2+3-block synthesis approach which involves imidate and sulfoxide glycosylation reactions. The preferred solution conformation of this structure was determined by using NMR spectroscopy and molecular dynamics simulations prior to carrying out quantitative structure-activity relationship studies in connection with the insulin signalling process. The ability of 1a to stimulate lipogenesis in rat adipocites as well as to inhibit cAMP dependent protein kinase and to activate pyruvate dehydrogenase phosphatase was investigated. Compound 1a did not show any significant activity, which may be taken as a strong indication that the GPI anchors are not the precursors of the IPG mediators.

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.