Efficient Synthesis of an α(2,9) Trisialic Acid by One-Pot Glycosylation and Polymer-Assisted Deprotection

An efficient synthesis of α(2,9) trisialic acid has been achieved via one-pot glycosylation and polymer-assisted deprotection. The synthesis involves chemo- and regioselective α-sialylation of ethylthiosialoside with the S-benzoxazolyl (S-Box) sialyl donor. Use of a prelinker to link an activated es...

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Bibliographic Details
Published inOrganic letters Vol. 10; no. 24; pp. 5597 - 5600
Main Authors Tanaka, Hiroshi, Tateno, Yusuke, Nishiura, Yuji, Takahashi, Takashi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.12.2008
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Glycosylation
Physical Sciences
Polymers - chemistry
Science & Technology
Sialic Acids - chemical synthesis
GLYCOSIDES
SIALOSIDES
STRATEGY
OLIGOSACCHARIDE SYNTHESIS
PHOSPHITE
SIALIC-ACID
DONORS
O-SIALYLATION
CLEAVAGE
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Summary:An efficient synthesis of α(2,9) trisialic acid has been achieved via one-pot glycosylation and polymer-assisted deprotection. The synthesis involves chemo- and regioselective α-sialylation of ethylthiosialoside with the S-benzoxazolyl (S-Box) sialyl donor. Use of a prelinker to link an activated ester and a vinyl ether via a carbon chain enables polymer-assisted deprotection of the protected trisialic acids.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol802207e