New Approaches to Analogs of Alpha-Linked Galactosylceramides Using Serinol

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New Approaches to Analogs of Alpha-Linked Galactosylceramides Using Serinol

Ulrike Jost 1 , Polina I. Abronina 2 , Alexander I. Zinin 2 , Udo Kragl 1,3 , Nikolay N. Kondakov 2 , Alexander O. Chizov 2 , Vladimir I. Torgov 2 , Leonid O. Kononov 2 , Dirk Michalik1,3

1 University of Rostock, Institute of Chemistry, Rostock, Germany, 2 N. D. Zelinsky Institute of Organic Chemistry, Moscow, Russian Federation, 3 Leibniz-Institut für Katalyse (LIKAT), Rostock, Germany

Serinol (2-amino-1,3-propanediol) (1), a glycerol derivative, can be generated by fermentation of glycerol, which is produced as byproduct from the biodiesel industry [1].

New derivatives of serinol, 3-[4-(2-chloroethoxy)benzyloxy]-2-phthalimidopropan-1-ol (2) 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 [2, 3].

It was found that NIS/AgOTf-promoted glycosylation of 3-[4-(2-chloroethoxy)benzyloxy]-2-phthalimidopropan-1-ol (2) with ethyl 4,6-O-(di-tert-butylsilylene)-1-thio-β-D-galactoside (3) resulted in both the expected α-linked diastereomeric glycosides 4a,b and the product of iodination of the benzyl group of the aglycon 5a,b. This process was avoided by using the corresponding galactosyl imidate under Et₃SiOTf promotion to give exclusively α-linked diastereomeric serinol glycosides [2].

Synthesis of galactosylceramide analogs starting from serinol (1).

This work was financially supported by “Fachagentur Nachwachsende Rohstoffe e.V. (FNR e.V.)” (grant no. 22005011) and the Russian Science Foundation (Project No. 16-13-10244-P).

Jost U.; Andreessen B.; Michalik D.; Steinbüchel A.; Kragl U.; Downstream processing of serinol from a glycerol-based fermentation broth and transfer to other amine containing molecules. Eng. Life Sci. 2017, 17, 479-488.

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. Russ. Chem. Bull. 2018, 67, 2297-2306.

Zinin A. I.; Stepanova E. V.; Jost U.; Kondakov N. N.; Shpirt A. M.; Chizhov A. O.; Torgov V. I.; Kononov L. O.; An efficient multigram-scale synthesis of 4-(ω-chloroalkoxy)phenols. Russ. Chem. Bull. 2017, 66, 304-312.

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