A simple access to the d-mannosidase inhibitor, 1-deoxymannojirimycin

Spreitz, Josef; Stütz, Arnold; Wrodnigg, Tanja

doi:10.1016/s0008-6215(01)00291-9

Cited by 21 publications

(13 citation statements)

References 22 publications

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“…The synthesis of DMJ 4 has been reported by Stütz and co-workers from D-fructose 78 [59] and influenced Florence Chery's choice of route to, this time a DMJ based peptidomimetic 81 from 78 via 79 and 80, using reductive amination, followed by N-benzylation (Scheme 13). [49a] Due to an interest in synthesis of carbohydrate based ligands for lectins, our laboratory were increasingly aware that glycosyl azides were useful synthetic intermediates and could be readily prepared in the laboratory.…”

Section: Chemical Approachesmentioning

confidence: 99%

Cyclisations and Strategies for Stereoselective Synthesis of Piperidine Iminosugars

Dhara

Bennett

Murphy

2021

The Chemical Record

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This personal account focuses on synthesis of polyhydroxylated piperidines, a subset of compounds within the iminosugar family. Cyclisations to form the piperidine ring include reductive amination, substitution via amines, iminium ions and cyclic nitrones, transamidification (N-acyl transfer), addition to alkenes, ring contraction and expansion, photoinduced electron transfer, multicomponent Ugi reaction and ring closing metathesis. Enantiomerically pure piperidines are obtained from chiral pool precursors (e. g. sugars, amino acids, Garner's aldehyde) or asymmetric reactions (e. g. epoxidation, dihydroxylation, aminohydroxylation, aldol, biotransformation). Our laboratory have contributed cascades based on reductive amination from glycosyl azide precursors as well as Huisgen azide-alkene cycloaddition. The latter's combination with allylic azide rearrangement has given substituted piperidines, including those with quaternary centres adjacent to nitrogen.

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Section: Chemical Approachesmentioning

confidence: 99%

Cyclisations and Strategies for Stereoselective Synthesis of Piperidine Iminosugars

Dhara

Bennett

Murphy

2021

The Chemical Record

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“…The levulinate groups were then removed selectively and substitution of the bromide for an azide group gave 37. Catalytic hydrogenation of 37, an intermediate related to that used by Stuetz and co-workers in their synthesis of 1-deoxymannojirimycin, [43] and subsequent N-benzylation gave the target DNJ derivative 30.…”

Section: Design and Synthesis Of Inhibitors Of Hiv-1 Proteasementioning

confidence: 99%

Peptidomimetics, Glycomimetics and Scaffolds from Carbohydrate Building Blocks

Murphy

2007

Eur J Org Chem

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Saccharides, due to their high density of functional groups and availability as chiral building blocks are scaffolds for bioactive compound discovery. Pyranosides and iminosugar‐based peptidomimetics have been synthesised as ligands for somatostatin receptors and HIV protease. The synthesis of polyhydroxylated macrolides related to natural products and cyclophanes has been achieved from carbohydrate fragments with a view to investigation of their potential as scaffolds. In addition, the trajectory of aromatic systems grafted to saccharides have been studied and this has led to the synthesis of probes for the study of carbohydrate protein interactions. These compounds include geometrically diverse bivalent glycomimetics derived from scaffolds that are hybrids of sugars and aromatic groups. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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“…Finally, hydrogenolysis of the protecting groups In this context, different syntheses of azasugars have also been reported starting from d-fructose. For example, Stütz et al [45] have reported an efficient synthesis of DMJ (10) in five steps from d-fructose in 14-17 % overall yield, as depicted in Scheme 8. Acetylated sugar 84, prepared from d- fructose in 55-60 % yield by partial acetylation, [46] was treated with commercially available dibromotriphenylphosphorane to give the expected open-chain bromosugar 85 in 89 % yield (only 30 % yield was obtained when using PBr 3 ).…”

Section: Chiral-pool Starting Materials: Carbohydratesmentioning

confidence: 99%

Recent Advances in the Total Synthesis of Piperidine Azasugars

et al. 2005

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Since the discovery of nojirimycin, a glycosidase inhibitor, polyhydroxylated piperidines (also called azasugars: the ring O‐atom of a carbohydrate is replaced by nitrogen) have attracted considerable attention and have been the target of numerous synthetic strategies during the last decade. The efficient synthesis of naturally occurring azasugars and their analogs is of considerable importance due to their potential glycosidase inhibitor properties. Some of them have been widely investigated as candidates for drugs to treat a variety of carbohydrate‐mediated diseases such as diabetes, viral infections, including HIV, cancer metastasis, hepatitis, and Gaucher’s disease. This microreview focuses on recent syntheses of azasugars. In addition, the biology of these compounds is briefly considered. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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A simple access to the d-mannosidase inhibitor, 1-deoxymannojirimycin

Cited by 21 publications

References 22 publications

Cyclisations and Strategies for Stereoselective Synthesis of Piperidine Iminosugars

Cyclisations and Strategies for Stereoselective Synthesis of Piperidine Iminosugars

Peptidomimetics, Glycomimetics and Scaffolds from Carbohydrate Building Blocks

Recent Advances in the Total Synthesis of Piperidine Azasugars

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