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Glycoscience pp 1913-1997 | Cite as

Carbasugars: Synthesis and Functions

  • Yoshiyuki Kobayashi

Abstract

It is well recognized that glycosidase inhibitors are not only tools to elucidate the mechanism of a living system manipulated by glycoconjugates but also potential clinical drugs and insecticides by inducing the failure of glycoconjugates to perform their function. In this chapter, the syntheses and functions of natural glycosidase inhibitors (cyclophelitol , allosamidine , and trehazoilin ), which possess highly oxygenated and functionalized cyclohexanes or cyclopentanes in their structures and are defined as carbasugars , and the structure and activity relationships (SAR) of their derivatives are described. Also, recently much attention has been focused on neuraminidase inhibitors as anti‐influenza drugs since relenza , which was derived from sialic acid, and also, tamiflu , which is the artificial carbasugar designed as a transition state analogue in the hydrolysis pathway of substrates by neuraminidase, were launched in the market. Herein, the medicinal chemistry efforts to discover tamiflu and some efficient syntheses applicable to process chemistry are described. Finally, useful synthetic methodologies for carbasugar formation from sugars are also introduced in this chapter.

Keywords

Carbasugars Cyclitols Glycosidase inhibitors Cyclophelitol Allosamidin Trehazolin Neuraminidase inhibitor Tamiflu Intramolecular [3+2] cycloaddition The Ferrier reaction 

Abbreviations

CDMA

catalytic desymmetrization of meso-aziridine

Chx

cyclohexyl

DBU

1,8-diazabicyclo[5.4.0]undec-7-ene

DDMPO

diisobutylaluminum 2,6-di-tert-butyl-4-methoxyphenoxide

DEIPS

diethylisopropylsilyl

DIBALH

diisobutylaluminum hydride

DIPEA

diisopropylethylamine

DMAP

N, N-dimethylaminopyridine

DMF

N, N-dimethylformamide

2,2-DMP

2,2-dimethoxypropane

DMSO

dimethylsulfoxide

HA

hemagglutinin

HPLC

high pressure liquid chromatography

KHMDS

potassium (1,1,1,3,3,3)-hexamethyldisilazide

mCPBA

m-chloroperbenzoic acid

MOM

methoxymethyl

NA

neuraminidase

NBA

N-bromoacetamide

NBS

N-bromosucciimide

NIS

N-iodosucciimide

NMO

4-methylmorpholine N-oxide

PPTS

pyridinium p-toluenesulfonate

RCM

ring-closing metathesis

SEMCl

2-(trimethylsilyl)ethoxymethyl chloride

TBAI

tetrabutylammonium iodide

TBAF

tetrabutylammonium fluoride

TBDMS

t-butyldimethylsilyl

TBDPSCl

t-butyldiphenylsilyl chloride

TFA

trifluoroacetic acid

TFAA

trifluoroacetic anhydride

THAB

tetrahexylammonium bromide

TMSCN

trimethylsilyl cyanide

Notes

Acknowledgements

Finally, I thank Dr. Masao Shiozaki, currently at RIKEN, for helpful discussions and suggestions during the preparation of this chapter.

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Copyright information

© Springer-Verlag Berlin Heidelberg New York 2008

Authors and Affiliations

  • Yoshiyuki Kobayashi
    • 1
  1. 1.Daiichi Sankyo Research InstituteLa JollaUSA

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