Carbohydrate research

Synthesis of 4-amino-4, 5-dideoxy-L-lyxofuranose derivatives and their evaluation as fucosidase inhibitors

C Chevrier, D Le Nouën, A Defoin, C Tarnus

Index: Chevrier, Carine; Le Nouen, Didier; Defoin, Albert; Tarnus, Celine Carbohydrate Research, 2011 , vol. 346, # 10 p. 1202 - 1211

Full Text: HTML

Citation Number: 12

Abstract

Abstract The nitrone 4 (4, 5-dideoxy-4-hydroxylamino-3, 4-O-isopropylidene-l-lyxofuranose) was synthesised from d-ribose and used as key intermediate for the preparation of fucosidase inhibitors. We describe two transformations of 4. Hydrolysis with aqueous sulfur dioxide gave the known potent nanomolar inhibitor 4-amino-4, 5-dideoxy-l-lyxofuranose (3). 1, 3-Dipolar cycloaddition with enol ethers led to the related 1, 2, 5, 6-tetradeoxy-2, 5- ...

Related Articles:

Nucleosides. 114. 5'-O-Glucuronides of 5-fluorouridine and 5-fluorocytidine. Masked precursors of anticancer nucleosides

[Watanabe, K. A.; Matsuda, A.; Halat, M. J.; Hollenberg, D. H.; Nisselbaum, J. S.; Fox, J. J. Journal of Medicinal Chemistry, 1981 , vol. 24, # 7 p. 893 - 897]

The Lewis Base-Catalyzed Silylation of Alcohols A Mechanistic Analysis

[Virtanen, Noora; Polari, Lauri; Vaelilae, Maria; Mikkola, Satu Journal of Physical Organic Chemistry, 2005 , vol. 18, # 5 p. 385 - 397]

The Lewis Base-Catalyzed Silylation of Alcohols A Mechanistic Analysis

[Virtanen, Noora; Polari, Lauri; Vaelilae, Maria; Mikkola, Satu Journal of Physical Organic Chemistry, 2005 , vol. 18, # 5 p. 385 - 397]

Simple approach to O-protected deaminotunicaminyluracil

[Karpiesiuk, Wojciech; Banaszek, Anna Tetrahedron, 1994 , vol. 50, # 9 p. 2965 - 2974]

The Lewis Base-Catalyzed Silylation of Alcohols A Mechanistic Analysis

[Virtanen, Noora; Polari, Lauri; Vaelilae, Maria; Mikkola, Satu Journal of Physical Organic Chemistry, 2005 , vol. 18, # 5 p. 385 - 397]

More Articles...