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 .
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 .
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.