Aziridine carboxylate from D-glucose: Synthesis of polyhydroxylated piperidine, pyrrolidine alkaloids and study of their glycosidase inhibition

Dilip D. Dhavale; K. S.Ajish Kumar; Vinod D. Chaudhari; Tarun Sharma; Sushma G. Sabharwal; J. Prakashareddy

doi:10.1039/b509216g

Aziridine carboxylate from D-glucose: Synthesis of polyhydroxylated piperidine, pyrrolidine alkaloids and study of their glycosidase inhibition

Dilip D. Dhavale, K. S.Ajish Kumar, Vinod D. Chaudhari, Tarun Sharma, Sushma G. Sabharwal, J. Prakashareddy

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37 Scopus citations

Abstract

The D-glucose derived aziridine carboxylate 5 was obtained from (E)-ethyl-6-bromo-1,2-O-isopropylidene-3-O-benzyl-5-deoxy-α-D-xylo-5-eno- heptofuranuronate 4 through conjugate addition of benzylamine and in situ intramolecular nucleophilic expulsion of bromine. The regioselective aziridine ring-opening, using water as a nucleophile, resulted in the α-hydroxy- β-aminoester 6, which was exploited in the synthesis of six and five membered azasugars 1b/1c and 2b/2c, respectively. The glycosidase inhibitory activity of the title compounds was evaluated.

Original language	English
Pages (from-to)	3720-3726
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	3
Issue number	20
DOIs	https://doi.org/10.1039/b509216g
State	Published - 21 Oct 2005
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Aziridine carboxylate from D-glucose: Synthesis of polyhydroxylated piperidine, pyrrolidine alkaloids and study of their glycosidase inhibition",

abstract = "The D-glucose derived aziridine carboxylate 5 was obtained from (E)-ethyl-6-bromo-1,2-O-isopropylidene-3-O-benzyl-5-deoxy-α-D-xylo-5-eno- heptofuranuronate 4 through conjugate addition of benzylamine and in situ intramolecular nucleophilic expulsion of bromine. The regioselective aziridine ring-opening, using water as a nucleophile, resulted in the α-hydroxy- β-aminoester 6, which was exploited in the synthesis of six and five membered azasugars 1b/1c and 2b/2c, respectively. The glycosidase inhibitory activity of the title compounds was evaluated.",

author = "Dhavale, {Dilip D.} and Kumar, {K. S.Ajish} and Chaudhari, {Vinod D.} and Tarun Sharma and Sabharwal, {Sushma G.} and J. Prakashareddy",

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T1 - Aziridine carboxylate from D-glucose

T2 - Synthesis of polyhydroxylated piperidine, pyrrolidine alkaloids and study of their glycosidase inhibition

AU - Dhavale, Dilip D.

AU - Kumar, K. S.Ajish

AU - Chaudhari, Vinod D.

AU - Sharma, Tarun

AU - Sabharwal, Sushma G.

AU - Prakashareddy, J.

PY - 2005/10/21

Y1 - 2005/10/21

N2 - The D-glucose derived aziridine carboxylate 5 was obtained from (E)-ethyl-6-bromo-1,2-O-isopropylidene-3-O-benzyl-5-deoxy-α-D-xylo-5-eno- heptofuranuronate 4 through conjugate addition of benzylamine and in situ intramolecular nucleophilic expulsion of bromine. The regioselective aziridine ring-opening, using water as a nucleophile, resulted in the α-hydroxy- β-aminoester 6, which was exploited in the synthesis of six and five membered azasugars 1b/1c and 2b/2c, respectively. The glycosidase inhibitory activity of the title compounds was evaluated.

AB - The D-glucose derived aziridine carboxylate 5 was obtained from (E)-ethyl-6-bromo-1,2-O-isopropylidene-3-O-benzyl-5-deoxy-α-D-xylo-5-eno- heptofuranuronate 4 through conjugate addition of benzylamine and in situ intramolecular nucleophilic expulsion of bromine. The regioselective aziridine ring-opening, using water as a nucleophile, resulted in the α-hydroxy- β-aminoester 6, which was exploited in the synthesis of six and five membered azasugars 1b/1c and 2b/2c, respectively. The glycosidase inhibitory activity of the title compounds was evaluated.

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Aziridine carboxylate from D-glucose: Synthesis of polyhydroxylated piperidine, pyrrolidine alkaloids and study of their glycosidase inhibition

Abstract

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