68601-72-9Relevant academic research and scientific papers
Dehydrative Glycosylation Enabled by a Comproportionation Reaction of 2-Aryl-1,3-dithiane 1-Oxide?
Cai, Lei,Zeng, Jing,Li, Ting,Xiao, Ying,Ma, Xiang,Xiao, Xiong,Zhang, Qin,Meng, Lingkui,Wan, Qian
supporting information, p. 43 - 49 (2019/11/28)
A new dehydrative glycosylation reaction has been established by capitalizing on the comproportionation reaction of 2-aryl-1,3-dithiane 1-oxides promoted by triflic anhydride (Tf2O). By wedding the high potency of thiophilic promoter system with the step efficiency of dehydrative glycosylation, this reagent underwent facile intermolecular oxothio acetalization with C1-hemiacetal donor to install a temporary leaving group, rendering a transient electrophilic center at the remote site to the anomeric position. The sulfenyl triflate tethered at the terminus concomitantly activated the sulfide intramolecularly to afford the oxocarbenium ion, thereby facilitating the title glycosylation. Aside from accommodating broad range functional groups and inactive hemiacetal substrates, the present activation protocol also proved expedient for 1,3-diol protection. Most importantly, this method further provided a fresh perspective for the application of sulfur chemistry to carbohydrate chemistry.
Solid-phase supported synthesis of the branched pentasaccharide moiety that occurs in most complex type N-glycan chains
Rademann, Joerg,Geyer, Armin,Schmidt, Richard R.
, p. 1241 - 1245 (2007/10/03)
Repetitive glycosylation on a sulfanylalkyl-functionalized Merrifield resin leads to the branched, complex pentasaccharide 1 in 20% overall yield in ten steps when appropriately protected O-glycosyl trichloroacetimidates are used as glycosyl donors. A dec
Syntheses of model oligosaccharides of biological significance. Synthesis of methyl 3,6-di-O-(alpha-D-mannopyranosyl)-alpha-d-mannopyranoside and the corresponding mannobiosides.
Winnik,Brisson,Carver,Krepinsky
, p. 15 - 28 (2007/10/02)
Methyl 2-O-allyl-4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl) -alpha-D-mannopyranoside (12) was prepared in 90% yield by Helferich glycosylation of methyl 2-O-allyl-4,6-O-benzylidene-alpha-D-mannopyranoside (9) with tetra-O-acetyl
SYNTHETIC STUDIES ON CELL SURFACE GLYCANS 3 BRANCHING PENTASACCHARIDES OF GLYCOPROTEIN
Ogawa, Tomoya,Katano, Kiyoaki,Sasajima, Kikuo,Matsui, Masanao
, p. 2779 - 2786 (2007/10/02)
Synthetic routes for the branching pentasaccharides 4 and 5 of glycoproteins are described in a regio- and stereo-controlled way.
SYNTHESIS OF A BRANCHED D-MANNOPENTAOSIDE AND A BRANCHED D-MANNOHEXAOSIDE: MODELS OF THE OUTER CHAIN OF THE GLYCAN OF SOYBEAN AGGLUTININ
Ogawa, Tomoya,Sasajima, Kikuo
, p. 53 - 66 (2007/10/02)
Synthetic routes are described to the D-mannopentaoside methyl 3-O-(3,6-di-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-6-O-α-D-mannopyranosyl-α-D-mannopyranoside and the D-mannohexaoside methyl 3-O-(3,6-di-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-6-O-(2-O-α-
