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

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

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2018, Volume: 67, Number: 12, Pages: 2297-2306 Pages count : 10 DOI: 10.1007/s11172-018-2373-3

Authors

Jost U. ¹ , Abronina P.I. ² , Zinin A.I. ² , Michalik D. ^1,3 , Kragl U. ¹ , Kondakov N.N. ² , Chizov A.O. ² , Torgov V.I. ² , Kononov L.O. ²

Affiliations

1	Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3A, 18059, Rostock, Germany
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
3	Leibniz Institute for Catalysis (LIKAT), Albert-Einstein-Str. 29a, 18059 Rostock, Germany

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.

Jost U. , Abronina P.I. , Zinin A.I. , Michalik D. , Kragl U. , Kondakov N.N. , Chizov A.O. , Torgov V.I. , Kononov L.O.
New approaches to analogs of α-linked galactosylceramides based on functionalized serinol
Russian Chemical Bulletin. 2018. V.67. N12. P.2297-2306. DOI: 10.1007/s11172-018-2373-3 WOS Scopus OpenAlex

Web of science:	WOS:000457425900026
Scopus:	2-s2.0-85061052805
OpenAlex:	W2913275083

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