New approaches to analogs of α-linked galactosylceramides based on functionalized serinol


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Аннотация

New derivatives of serinol, 3-[4-(2-chloroethoxy)benzyloxy]-2-phthalimidopropan-1-ol and 3-[4-(2-azidoethoxy)phenoxy]-2-phthalimidopropan-1-ol, were synthesized and tested as glycosyl acceptors in stereoselective 1,2-cis-galactosylation in the benzyl-free synthesis of analogs of α-linked galactosylceramides. It was found that NIS/AgOTf-promoted glycosylation of 3-[4-(2-chloroethoxy)benzyloxy]-2-phthalimidopropan-1-ol with ethyl 4,6-O-(di-tert-butylsilylene)-1-thio-β-D-galactoside resulted in both the expected α-linked diastereomeric glycosides and the product of iodination of the benzyl group of the aglycon. This process was avoided by using the corresponding galactosyl imidate under Et3SiOTf promotion to give exclusively α-linked diastereometic serinol glycosides.

Авторлар туралы

U. Jost

Institut für Chemie, Universität Rostock

Email: leonid.kononov@gmail.com
Германия, Albert-Einstein-Str. 3A, Rostock, 18059

P. Abronina

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

Email: leonid.kononov@gmail.com
Ресей, 47 Leninsky prosp., Moscow, 119991

A. Zinin

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

Email: leonid.kononov@gmail.com
Ресей, 47 Leninsky prosp., Moscow, 119991

D. Michalik

Institut für Chemie, Universität Rostock; Leibniz Institute for Catalysis (LIKAT)

Хат алмасуға жауапты Автор.
Email: dirk.michalik@uni-rostock.de
Германия, Albert-Einstein-Str. 3A, Rostock, 18059; Albert-Einstein-Str. 29a, Rostock, 18059

U. Kragl

Institut für Chemie, Universität Rostock

Email: leonid.kononov@gmail.com
Германия, Albert-Einstein-Str. 3A, Rostock, 18059

N. Kondakov

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

Хат алмасуға жауапты Автор.
Email: leonid.kononov@gmail.com
Ресей, 47 Leninsky prosp., Moscow, 119991

A. Chizov

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

Email: leonid.kononov@gmail.com
Ресей, 47 Leninsky prosp., Moscow, 119991

V. Torgov

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

Email: leonid.kononov@gmail.com
Ресей, 47 Leninsky prosp., Moscow, 119991

L. Kononov

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

Email: leonid.kononov@gmail.com
Ресей, 47 Leninsky prosp., Moscow, 119991

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