Synthesis and glycosidase-inhibitory activity of cyclophellitol analogues

Vincent W.-F. Tai; P. H. Fung; Y. S. Wong; Tony K.M. Shing

doi:10.1016/0957-4166(94)80177-0

Synthesis and glycosidase-inhibitory activity of cyclophellitol analogues

Vincent W.-F. Tai, P. H. Fung, Y. S. Wong, Tony K.M. Shing

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

Abstract

The 6-deoxy-1,2-anhydro-analogues of cyclophellitol, 5 and 6, have been synthesised from diol 11 via a regioselective ring opening of the cyclic sulfate 15, an internal S_N2 reaction and hydrogenolysis. Compounds 5, 6, cyclophellitol 1 and its diastereoisomers 2-4 were assayed for inhibitory activity against six glycosidases. Oxirane 5 was shown to possess activity towards both β-mannosidase (A. oryzae) and β-glucosidase (almonds) but 6 showed no significant inhibitory activity.

Original language	English
Pages (from-to)	1353-1362
Number of pages	10
Journal	Tetrahedron: Asymmetry
Volume	5
Issue number	7
DOIs	https://doi.org/10.1016/0957-4166(94)80177-0
Publication status	Published - 1994 Jul

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1016/0957-4166(94)80177-0

Cite this

@article{45d7ff215599473389cd20267686a336,

title = "Synthesis and glycosidase-inhibitory activity of cyclophellitol analogues",

abstract = "The 6-deoxy-1,2-anhydro-analogues of cyclophellitol, 5 and 6, have been synthesised from diol 11 via a regioselective ring opening of the cyclic sulfate 15, an internal SN2 reaction and hydrogenolysis. Compounds 5, 6, cyclophellitol 1 and its diastereoisomers 2-4 were assayed for inhibitory activity against six glycosidases. Oxirane 5 was shown to possess activity towards both β-mannosidase (A. oryzae) and β-glucosidase (almonds) but 6 showed no significant inhibitory activity.",

author = "{W.-F. Tai}, Vincent and Fung, {P. H.} and Wong, {Y. S.} and Shing, {Tony K.M.}",

year = "1994",

month = jul,

doi = "10.1016/0957-4166(94)80177-0",

language = "English",

volume = "5",

pages = "1353--1362",

journal = "Tetrahedron Asymmetry",

issn = "0957-4166",

publisher = "Elsevier Limited",

number = "7",

}

TY - JOUR

T1 - Synthesis and glycosidase-inhibitory activity of cyclophellitol analogues

AU - W.-F. Tai, Vincent

AU - Fung, P. H.

AU - Wong, Y. S.

AU - Shing, Tony K.M.

PY - 1994/7

Y1 - 1994/7

N2 - The 6-deoxy-1,2-anhydro-analogues of cyclophellitol, 5 and 6, have been synthesised from diol 11 via a regioselective ring opening of the cyclic sulfate 15, an internal SN2 reaction and hydrogenolysis. Compounds 5, 6, cyclophellitol 1 and its diastereoisomers 2-4 were assayed for inhibitory activity against six glycosidases. Oxirane 5 was shown to possess activity towards both β-mannosidase (A. oryzae) and β-glucosidase (almonds) but 6 showed no significant inhibitory activity.

AB - The 6-deoxy-1,2-anhydro-analogues of cyclophellitol, 5 and 6, have been synthesised from diol 11 via a regioselective ring opening of the cyclic sulfate 15, an internal SN2 reaction and hydrogenolysis. Compounds 5, 6, cyclophellitol 1 and its diastereoisomers 2-4 were assayed for inhibitory activity against six glycosidases. Oxirane 5 was shown to possess activity towards both β-mannosidase (A. oryzae) and β-glucosidase (almonds) but 6 showed no significant inhibitory activity.

UR - http://www.scopus.com/inward/record.url?scp=0028106554&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0028106554&partnerID=8YFLogxK

U2 - 10.1016/0957-4166(94)80177-0

DO - 10.1016/0957-4166(94)80177-0

M3 - Article

AN - SCOPUS:0028106554

SN - 0957-4166

VL - 5

SP - 1353

EP - 1362

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 7

ER -

Synthesis and glycosidase-inhibitory activity of cyclophellitol analogues

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this