Steric control of N-acetylgalactosamine in glycosidic bond formation

N-Acetylgalactosamine, protected with a 4,6-cyclic acetal followed by selective acylation at 3-OH, provides an excellent donor for the synthesis of α-glycosides, particularly the cancer associated antigens such as Tn, TF, Sialyl-Tn and Sialyl-TF. This fast and efficient synthesis is easily adaptable...

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Bibliographic Details
Published inTetrahedron letters Vol. 36; no. 38; pp. 6839 - 6842
Main Authors Yule, John E., Wong, Ting C., Gandhi, Sham S., Qiu, Dongxu, Riopel, Marc A., Rao Koganty, R.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 18.09.1995
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PROGNOSIS
CANCER
TN
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Summary:N-Acetylgalactosamine, protected with a 4,6-cyclic acetal followed by selective acylation at 3-OH, provides an excellent donor for the synthesis of α-glycosides, particularly the cancer associated antigens such as Tn, TF, Sialyl-Tn and Sialyl-TF. This fast and efficient synthesis is easily adaptable for commercial production of mucin type glycopeptides with O-linked carbohydrate structures which are currently being investigated as vaccines against cancers.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(95)01442-K