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Silylene/Oxazolidinone Double‐Locked Sialic Acid Building Blocks for Efficient Sialylation Reactions in Dichloromethane
Author(s) -
Hanashima Shinya,
Sato Kenichi,
Ito Yukishige,
Yamaguchi Yoshiki
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900543
Subject(s) - chemistry , sialic acid , block (permutation group theory) , silylene , dichloromethane , combinatorial chemistry , selectivity , organic chemistry , biochemistry , catalysis , geometry , mathematics , solvent , silicon
We describe efficient sialylation reactions in CH 2 Cl 2 with the use of silylene/oxazolidinone double‐locked sialic acid building blocks. The building blocks were synthesized from 4,5‐oxazolidinone‐protected phenylthiosialoside. In sialylation reactions towards primary and relatively reactive secondary hydroxy groups on the galactosides, the double‐locked building blocks provided desired coupling products in good yields with excellent α‐selectivities. In the sialylation reaction with the C3‐OH of the galactoside, the double‐locked building blocks expressed significantly better α‐selectivity in comparison with the results obtained by using the oxazolidinone‐locked building block. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)