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Cited by 24 publications
(20 citation statements)
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“…71,41 In my laboratory, we synthesised a pseudodisaccharide based on 3-substituted glucose (244) by coupling of a carbasugar C-1 alcohol (232) with an allo 3-triflate (235) ( Table 11, entry 9). 72 The yields for the synthesis of (1?6)-and (1?4)-linked compounds, at least, are high, and apparently independent of the structure of the nucleophile, from which we may infer that this approach may be used to synthesise other carbasugar pseudodisaccharides linked (1?4) or (1?6) to glucose. This approach to pseudodisaccharides requires triflates that will not easily undergo 1,2-elimination even under strongly basic conditions, so if further such carbohydrate triflates are discovered, the method may be extended to other linkages.…”
Section: Triflate Displacementmentioning
confidence: 99%
“…71,41 In my laboratory, we synthesised a pseudodisaccharide based on 3-substituted glucose (244) by coupling of a carbasugar C-1 alcohol (232) with an allo 3-triflate (235) ( Table 11, entry 9). 72 The yields for the synthesis of (1?6)-and (1?4)-linked compounds, at least, are high, and apparently independent of the structure of the nucleophile, from which we may infer that this approach may be used to synthesise other carbasugar pseudodisaccharides linked (1?4) or (1?6) to glucose. This approach to pseudodisaccharides requires triflates that will not easily undergo 1,2-elimination even under strongly basic conditions, so if further such carbohydrate triflates are discovered, the method may be extended to other linkages.…”
Section: Triflate Displacementmentioning
confidence: 99%
“…Related approaches have been used for the synthesis of thiooligosaccharides; carbohydrate sulfonates have been displaced either by thioacetate to introduce sulfur, or by an anomeric thiol for thiodisaccharide formation. [15] We converted some partially protected carbohydrates 1-6 [16][17][18][19][20][21] to their triflates 8-12 [22][23][24][25][26] or mesylate (7). In many cases, heating the sulfonates with potassium thioacetate in DMF gave a clean and high-yielding conversion to the thioacetates 13-17 with inversion of configuration (Scheme 1).…”
Section: Synthesismentioning
confidence: 99%
“…This is in marked contrast to the behaviour of reactions for the formation of similar N-linked structures, where the more stringent steric and electronic demands of a secondary centre over a primary centre (in a carbohydrate) appear to strongly disfavour the formation of pseudodisaccharides with secondary amine linkages involving even just one secondary centre. [7] We also investigated a streamlined synthesis of C 2 -symmetric thioether pseudodisaccharides using a divalent sulfur anion as nucleophile to dimerise a sulfonate electrophile, based on previous work for (1-1)-linked thiodisaccharide synthesis. [31,32] Treatment of carbohydrate triflates with dried sodium sulfide in acetonitrile with molecular sieves gave the dimers in generally very good yield for those triflates that give a clean S N 2 reaction with thioacetate (i.e.…”
Section: Synthesismentioning
confidence: 99%
See 1 more Smart Citation
“…[15] To test this hypothesis, we have synthesised a number of pseudodisaccharides by Mitsunobu chemistry or epoxideopening reactions. [16] The products of epoxide opening are α-altrosides with amino substitution at either the 2-or 3-position. In addition, pseudodisaccharides substituted at the 6-position were also synthesised.…”
Section: Introductionmentioning
confidence: 99%