1. C-Glycoside D-galacturonates suitable as glycosyl acceptors for the synthesis of allyl C-homo- and rhamno-galacturonan modules.
- Author
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Farouk, Mahmoud, Michalik, Dirk, Villinger, Alexander, and Vogel, Christian
- Subjects
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GLYCOSYLATION kinetics , *GALACTURONAN , *DISACCHARIDES synthesis , *RHAMNOGALACTURONANS , *STEREOSELECTIVE reactions - Abstract
Methyl 2,3-di-O-benzyl-1-deoxy-1-(prop-2-enyl)-α-D-galactopyranuronate and benzyl 2,3-di-Obenzyl- 1-deoxy-1-(prop-2-enyl)-α-D-galactopyranuronate were prepared as glycosyl acceptors. The glycosyl donors benzyl 4-O-acetyl-2,3-di-O-benzyl-1-(trichloroacetimidoyloxy)-α-Dgalactopyranosyluronate and benzyl 4-O-acetyl-2,3-di-O-benzyl-1-(trichloroacetimidoyloxy)-β- D-galactopyranosyluronate were synthesized in 98% and 76% yields respectively. Disaccharides methyl (methyl 4-O-acetyl-2,3-di-O-benzyl-α/β-D-galactopyranosyluronate)-(1→4)-2,3-di-Obenzyl- 1-deoxy-1-(prop-2-enyl)-α-D-galactopyranuronate and benzyl (benzyl 4-O-acetyl-2,3-di- O-benzyl-α/β-D-galactopyranosyluronate)-(1→4)-2,3-di-O-benzyl-1-deoxy-1-(prop-2-enyl)-α-Dgalactopyranuronate were synthesized in 53% and 44% yields respectively and with moderate stereoselectivity. The synthesis of 1,2-O-acetyl-3,4-di-O-benzyl-L-rhamnopyranose (α/β) and 2- O-acetyl-1-bromo-3,4-di-O-benzyl-α-L-rhamnopyranosyl suitable as glycosyl donors is described. The disaccharide methyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→4)- 2,3-di-O-benzyl-1-deoxy-1-(prop-2-enyl)-α-D-galactopyranuronate, and benzyl (2-O-acetyl-3,4- di-O-benzyl-α-L-rhamnopyranosyl)-(1→4)-2,3-di-O-benzyl-1-deoxy-1-(prop-2-enyl)-α-D-galactopyranuronate were obtained in 54% and 56% yield respectively. [ABSTRACT FROM AUTHOR]
- Published
- 2013