caa a22 4500 469115149 CHVBK 20180323133122.0 cr unu---uuuuu 170328e19920601xx s 000 0 eng 10.1007/BF00780758 doi (NATIONALLICENCE)springer-10.1007/BF00780758 Synthesis of O -glycopyranosyl- N -hydroxysuccinimides of glucose and lactose and their opening by nucleophiles into prespacer glycosides [Elektronische Daten] [Mats Andersson, Stefan Oscarson] O-Glycopyranosyl-N-hydroxysuccinimides of glucose and lactose have been synthesized. Peracetylated sugars, acetobromo sugars and benzoylated thioethyl glycosides have been used as precursors. With boron trifluoride etherate in dichloromethane, peracetylated sugars gave predominantly the β anomer. Trimethylsilyl trifluoromethanesulfonate in nitromethane, however, gave predominantly the α anomer. Treatment of the acetylatedO-glucopyranosyl-N-hydroxysuccinimide with various nucleophiles (methoxide, hydroxide and pentylamine) gave the corresponding deacetylatedN-(succinyl)glucopyranosylhydroxylamines in almost quantitative yield. These derivatives are suitable for the formation of glycoconjugates or attachment of carbohydrates to solid phases using the opened succinimide as linking arm. Chapman & Hall, 1992 N -Hydroxysuccinimide nationallicence O -glycosylhydroxylamide nationallicence spacer nationallicence glycoconjugates nationallicence Andersson Mats Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91, Stockholm, Sweden aut Oscarson Stefan Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91, Stockholm, Sweden aut Glycoconjugate Journal Kluwer Academic Publishers 9/3(1992-06-01), 122-125 0282-0080 9:3<122 1992 9 10719 https://doi.org/10.1007/BF00780758 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF00780758 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Andersson Mats Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91, Stockholm, Sweden aut NATIONALLICENCE 700 1- Oscarson Stefan Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91, Stockholm, Sweden aut NATIONALLICENCE 773 0- Glycoconjugate Journal Kluwer Academic Publishers 9/3(1992-06-01), 122-125 0282-0080 9:3<122 1992 9 10719 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer