Total syntheses of glucosidase inhibitors, cyclophellitols

A β-d-glucosidase inhibitor, cyclophellitol [(1S,2R,3S,4R,5R,6R)-5-hydroxymethyl-7-oxabicyclo[4.1.0]heptane-2,3,4-triol, 1] and its epoxide diastereomer, 1,6-epicyclophellitol (2) have been synthesized by using an intramolecular [3+2]-cycloaddition of a nitrile oxide to an alkene as a key step. 2,3,...

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Bibliographic Details
Published in:Carbohydrate research 1991-12, Vol.222, p.189-203
Main Authors: Tatsuta, Kuniaki, Niwata, Yoshihisa, Umezawa, Kazuo, Toshima, Kazunobu, Nakata, Masaya
Format: Article
Language:English
Subjects:
beta-glucosidase
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
chemical reactions
Chemistry
enzyme inhibitors
Exact sciences and technology
Organic chemistry
Preparations and properties
stereochemistry
synthesis
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Summary:A β-d-glucosidase inhibitor, cyclophellitol [(1S,2R,3S,4R,5R,6R)-5-hydroxymethyl-7-oxabicyclo[4.1.0]heptane-2,3,4-triol, 1] and its epoxide diastereomer, 1,6-epicyclophellitol (2) have been synthesized by using an intramolecular [3+2]-cycloaddition of a nitrile oxide to an alkene as a key step. 2,3,4-Tri-O-benzyl-6,7-dideoxy-d-ido-hept- 6-enose (E,Z)-oxime (6) was prepared from l-glucose in 11 steps. Intramolecular cycloaddition of 6 was realized by NaOCl via an intermediary nitrile oxide to afford the isoxazoline, (1S,2R,3S,4S,5R)-3,4,5-tribenzyloxy-2-hydroxy-8-oxa-7-azabicyclo[4.3.0]non-6-ene (7). Hydrogenolysis of 7 followed by a 5-step sequence gave cyclophellitol (1). Compound 2 was synthesized from methyl δ-d-galactopyranoside by using a conceptually similar route. The glycosidase-inhibiting activities of 2 were examined.
ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(91)89017-A