1989
DOI: 10.1016/0008-6215(89)85184-5
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Branched thiocyclomalto-oligosaccharides: Synthesis and properties of 6-S-α- and 6-S-β-d-glucopyranosyl-6- thiocyclomaltoheptaose

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Cited by 34 publications
(15 citation statements)
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“…Monovalent cyclodextrin neoglycoconjugates : The key precursor for the preparation of monobranched β ‐CD neoglycoconjugates is 6 I ‐deoxy‐6 I ‐ O‐para ‐tolylsulfonylcyclomaltoheptaose ( 1 ), for which we have recently reported an improved one‐step synthesis from β ‐CD 8. Its reactivity was first exploited by Defaye's group in the preparation of 6 I ‐ S ‐glycosyl‐6 I ‐thiocyclomaltoheptaose ( 4 ) by use of the sodium salt of 1‐thio‐ α ‐ and β ‐ D ‐glucopyranose as the nucleophile9 and was further extended to the synthesis of the analogous monovalent α ‐ and β ‐thiomaltosyl β ‐CD conjugates10 (Scheme ).…”
Section: Discussionmentioning
confidence: 99%
“…Monovalent cyclodextrin neoglycoconjugates : The key precursor for the preparation of monobranched β ‐CD neoglycoconjugates is 6 I ‐deoxy‐6 I ‐ O‐para ‐tolylsulfonylcyclomaltoheptaose ( 1 ), for which we have recently reported an improved one‐step synthesis from β ‐CD 8. Its reactivity was first exploited by Defaye's group in the preparation of 6 I ‐ S ‐glycosyl‐6 I ‐thiocyclomaltoheptaose ( 4 ) by use of the sodium salt of 1‐thio‐ α ‐ and β ‐ D ‐glucopyranose as the nucleophile9 and was further extended to the synthesis of the analogous monovalent α ‐ and β ‐thiomaltosyl β ‐CD conjugates10 (Scheme ).…”
Section: Discussionmentioning
confidence: 99%
“…[37][38][39][40][41][42] Tosylation at O-6 I is favored on steric grounds and, in the particular case of bCD when using aqueous media, by inclusion of the sulfonylating reagent in the cavity. This pathway competes, however, with tosylation at the more acidic O-2 position, which strongly complicates the purification step and represents a serious handicap for the final yield.…”
Section: Position-selective Multivalent Cyclodextrin Conjugatesmentioning
confidence: 99%
“…[8] Its reactivity was first exploited by Defaye×s group in the preparation of 6 I -S-glycosyl-6 Ithiocyclomaltoheptaose (4) by use of the sodium salt of 1-thio-a-and b-d-glucopyranose as the nucleophile [9] and was further extended to the synthesis of the analogous monovalent aand b-thiomaltosyl b-CD conjugates [10] (Scheme 1).…”
Section: Discussionmentioning
confidence: 99%