Organic Syntheses 2003
DOI: 10.1002/0471264180.os077.23
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6 A ‐O‐p‐Toluenesulfonyl‐β‐Cyclodextrin

Abstract: 6 A ‐O‐p‐toluenesulfonyl‐β‐cyclodextrin product: 6 A ‐O‐p‐toluenesulfonyl‐β‐cyclodextrin product: Cyclodextrin monotosylate

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Cited by 37 publications
(48 citation statements)
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“…[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%
“…[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%
“…To a solution of 3-mercaptopropanoic acid (14.6 µL, 0.168 mmol) in DMF (2 mL) sodium hydride (15 mg, 0.620 mmol) was added in 10 equal portions and the mixture was stirred for 1 h. Then 6-mono-p-toluenesulfonyl-β-cyclodextrin 30 (100 mg, 0.077 mmol) was added and the whole was stirred at 100 o C for 2 h. The mixture was allowed to cool to room temperature and then water was added (2 mL). The solvent was driven off under vacuum, the compound was dissolved in minimum volume of water, the pH was adjusted to 7 and the solution was dialysed for 1 day.…”
Section: Mono[6-(carboxyethylthio)-6-deoxy]-β-cyclodextrin (7)mentioning
confidence: 99%
“…Blocking Aβ production has targeted BACE [123], γ-secretase inhibitors [124], modulating APP synthesis, [125] and the upregulation of α-secretase [126]. However, the role of APP, Aβ , and the secretases in normal physiological function [127][128][129][130] presents a problem in providing effective and safe approaches to AD therapy. As we have described above, APP has neuroprotective properties that may be mediated by cGMP/PKG signaling [50].…”
Section: Relevance To the Amyloid Cascadementioning
confidence: 99%