(1S,2S,7R,8aS)- and (1S,2S,7S,8aS)-trihydroxyoctahydroindolizine: Two new glycosidase inhibitors by nitrone cycloaddition strategy

Goti, Andrea; Cardona, Francesca; Brandi, Alberto; Picasso, Sylviane; Vogel, Pierre

doi:10.1016/0957-4166(96)00200-5

Cited by 71 publications

(24 citation statements)

References 62 publications

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“…10 d). When switching to chiral (S,S)-3,4-bis(dimethyl-tert-butylsilyloxy)pyrrolidine derivative 15, [18] chloride 12 or triflate 13 were slowly converted into diastereoisomeric DMAP-paracyclophane 16 (Scheme 5). Conversion was complete after 15 d at 150°C in toluene in a sealed tube.…”

Section: Resultsmentioning

confidence: 99%

DMAP‐[2.2]paracyclophane: Observation of an Unusual C–C Insertion

et al. 2011

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Section: Resultsmentioning

confidence: 99%

DMAP‐[2.2]paracyclophane: Observation of an Unusual C–C Insertion

et al. 2011

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“…This results is superior to those previously reported in the literature, in which the corresponding hydroxylamine was oxidized to the nitrone with SeO 2 as catalyst. [24] The directed oxidation of the secondary amine bearing O-MOM protecting groups has been reported as well, but in this case stoichiometric amounts of the much less "green" HgO were used. [25] Another cyclic nitrone 5i, originating from oxidation of (S)-proline methyl ester (3i), was obtained with complete regiocontrol and in high yield, much higher than that previously reported (73 % vs. 45 %; Table 4, Entry 9).…”

Section: Scope Of the Reactionmentioning

confidence: 99%

Effective Oxidation of Secondary Amines to Nitrones with Alkyl Hydroperoxides Catalysed by (Trialkanolaminato)titanium(IV) Complexes

et al. 2010

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The effective catalytic oxidation of secondary amines to nitrones with alkyl hydroperoxides as the primary oxidants is described. The titanium alkoxide catalysts are protected from the water co-product by the combined use of a tightly binding trialkanolamine ligand and molecular sieves. Nitrones can be obtained in high yields (up to 98%) under homogeneous, anhydrous conditions and even in the absence of solvent. The reactions are fast (2-7 h) and good selectivity and complete conversion can be achieved with as little as 1% catalys

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“…Vogel et al developed a coupling strategy between a pyrrolidine aldehyde 213 and a sugar enol triflate 214 for the synthesis of (1-3) linked aza-C-disaccharides such as 195 and 196 [143,[149][150][151][152][153]. The methodology was also applied for the synthesis of C-disaccharides with a hydroxymethylene linkage.…”

Section: Scheme (20)mentioning

confidence: 99%

C-Glycosides and Aza-C-Glycosides as Potential Glycosidase and Glycosyltransferase Inhibitors

Zou¹

2005

CTMC

146

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Glycosylation as one of most important post-translational modification of gene products is often critical to specific cellular biological functions. Since elevated glycoprocessing enzyme activities have been implicated in the development of various diseases including cancer metastasis, glycosidases and glycosyltransferases are considered as therapeutic targets. Azasugars, the first generation of enzyme inhibitors, have been extensively investigated and two azasugar-based drugs (Miglitol and Miglustat) have been approved. Aza-C-glycosides, molecules with an azasugar core and various C-aglycons attached at the pseudo anomeric center, have the potential to become the second-generation inhibitors with improved specificity and membrane permeability. In this review, C-glycosides, aza-C-glycosides, and aza-C-disaccharides are introduced as glycoprocessing enzyme inhibitors. The synthetic approaches toward those molecules are described based on the key reactions, which include reductive amination, nucleophilic ring opening of epoxides, nucleophilic addition to imines (C=N), and hetero-Michael additions. Aza-C-glycoside-based libraries are also described for the discovery of promising second-generation inhibitors.

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(1S,2S,7R,8aS)- and (1S,2S,7S,8aS)-trihydroxyoctahydroindolizine: Two new glycosidase inhibitors by nitrone cycloaddition strategy

Cited by 71 publications

References 62 publications

DMAP‐[2.2]paracyclophane: Observation of an Unusual C–C Insertion

DMAP‐[2.2]paracyclophane: Observation of an Unusual C–C Insertion

Effective Oxidation of Secondary Amines to Nitrones with Alkyl Hydroperoxides Catalysed by (Trialkanolaminato)titanium(IV) Complexes

C-Glycosides and Aza-C-Glycosides as Potential Glycosidase and Glycosyltransferase Inhibitors

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