Synthesis of polyhydroxylated azetidine iminosugars and 3-hydroxy-N-methylazetidine-2-carboxylic acid from d-glucose

Lawande, Pravin P.; Sontakke, Vyankat A.; Nair, Roopa J.; Khan, Ayesha; Sabharwal, Sushma G.; Shinde, Vaishali

doi:10.1016/j.tet.2015.05.057

Cited by 14 publications

(2 citation statements)

References 48 publications

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“…Azetidines are an important class of four-membered ring systems in modern synthetic chemistry. 1,2 They have received much attention as starting precursors in the synthesis of several nitrogen-containing compounds of synthetic [3][4][5][6] and biological [7][8][9] interest. Furthermore, these small heterocycles are of great interest since they represent the structural core of various natural products and pharmaceutical agents.…”

Section: Introductionmentioning

confidence: 99%

A simple and general synthetic route to N-alkylazetidines from 1,2-amino alcohols

BESBES¹,

Kaabi²,

Slema³

et al. 2022

Arkivoc

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Azetidines and their derivatives are of major interest since they exhibit important biological activities besides their utility as synthetic intermediates. Herein we describe a mild and efficient method for the formation of functionalized N-alkyl-azetidines in moderate-to-good yields starting from 1,2-aminoalcohols. This azetidine synthesis proceeds through three steps involving O-methylation of the starting 1,2-amino alcohols, reduction of the ester group of the resulting 1,2-aminoethers, and subsequent mesylation/intracyclization of the 1,3amino alcohol intermediates.

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Section: Introductionmentioning

confidence: 99%

A simple and general synthetic route to N-alkylazetidines from 1,2-amino alcohols

BESBES¹,

Kaabi²,

Slema³

et al. 2022

Arkivoc

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“…Brigaud et al 21 Polyhydroxylated nitrogen containing compounds popularly known as iminosugars are well known glycosidase inhibitors. 23,24 Shinde et al 25 have developed a convenient methodology for the synthesis of azetidine iminosugars and 3-hydroxy-N-methylazetidine-2-carboxylic acid from D-glucose using intramolecular Mitsunobu reaction. The synthetic methodology involved the treatment of azido aldehyde 76 with sodium borohydride in aqueous methanol at 0 C to afford the corresponding azido alcohol 77.…”

Section: Introductionmentioning

confidence: 99%

Recent advances in synthetic facets of immensely reactive azetidines

et al. 2017

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Synthesis of Chiral Tetrasubstituted Azetidines from Donor–Acceptor Azetines via Asymmetric Copper(I)‐Catalyzed Imido‐Ylide [3+1]‐Cycloaddition with Metallo‐Enolcarbenes

et al. 2019

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The all-cis stereoisomers of tetrasubstituted azetidine-2-carboxylic acids and derivatives that possess three chiral centers have been prepared in high yield and stereocontrol from silyl-protected Z-g-substituted enoldiazoacetates and imido-sulfur ylides by asymmetric [3+ +1]-cycloaddition using chiral sabox copper(I) catalysis followed by Pd/C catalytic hydrogenation. Hydrogenation of the chiral p-methoxybenzyl azetine-2-carboxylates occurs with both hydrogen addition to the C = Cbond and hydrogenolysis of the ester.

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Synthesis of polyhydroxylated azetidine iminosugars and 3-hydroxy-N-methylazetidine-2-carboxylic acid from d-glucose

Cited by 14 publications

References 48 publications

A simple and general synthetic route to N-alkylazetidines from 1,2-amino alcohols

A simple and general synthetic route to N-alkylazetidines from 1,2-amino alcohols

Recent advances in synthetic facets of immensely reactive azetidines

Synthesis of Chiral Tetrasubstituted Azetidines from Donor–Acceptor Azetines via Asymmetric Copper(I)‐Catalyzed Imido‐Ylide [3+1]‐Cycloaddition with Metallo‐Enolcarbenes

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