N,N-Diacetylsialyl chloride—a novel readily accessible sialyl donor in reactions with neutral and charged nucleophiles in the absence of a promoter Full article
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Carbohydrate Research
ISSN: 1873-426X , E-ISSN: 0008-6215 |
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| Output data | Year: 2010, Volume: 345, Number: 6, Pages: 721-730 Pages count : 10 DOI: 10.1016/j.carres.2010.01.005 | ||
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Abstract:
N,N-Diacetylneuraminic acid glycosyl chloride was prepared for the first time and made to react with various nucleophiles to give the corresponding α-glycosyl phosphate, β-glycosyl dibenzyl phosphate, α-glycosyl azide, α-phenyl thioglycoside and α-glycosyl xanthate in 65–82% yields and high stereoselectivity while its reactions with simple alcohols were not stereoselective. The new sialyl donor made possible the first stereoselective synthesis of sialic acid glycosyl phosphate with α-configuration and highly efficient synthesis of β-configured sialic acid glycosyl dibenzyl phosphate.
Cite:
Orlova A.V.
, Shpirt A.M.
, Kulikova N.Y.
, Kononov L.O.
N,N-Diacetylsialyl chloride—a novel readily accessible sialyl donor in reactions with neutral and charged nucleophiles in the absence of a promoter
Carbohydrate Research. 2010. V.345. N6. P.721-730. DOI: 10.1016/j.carres.2010.01.005 WOS Scopus OpenAlex
N,N-Diacetylsialyl chloride—a novel readily accessible sialyl donor in reactions with neutral and charged nucleophiles in the absence of a promoter
Carbohydrate Research. 2010. V.345. N6. P.721-730. DOI: 10.1016/j.carres.2010.01.005 WOS Scopus OpenAlex
Identifiers:
| Web of science: | WOS:000277112800001 |
| Scopus: | 2-s2.0-77949566811 |
| OpenAlex: | W1996392997 |