β-L-Arabinofuranosylation Conducted by 5-O-(2-pyridinecarbonyl)-L-arabinofuranosyl Trichloroacetimidate

• Published in: Carbohydrate research Vol. 460; pp. 1 - 7
• Main Authors: Li, Hong-Zhan, Ding, Jie, Cheng, Chun-Ru, Chen, Yue, Liang, Xing-Yong
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 02.05.2018; Elsevier
• Subjects: Acetamides - chemistry; Arabinose - chemistry; Biochemistry & Molecular Biology; Chemistry; Chemistry, Applied; Chemistry, Organic; Chloroacetates - chemistry; Glycosylation; HAD effect; Life Sciences & Biomedicine; One-pot synthesis; Physical Sciences; Science & Technology; β-Arabinofuranosylation; β-L-Araf-L-Hyp4; HAD effect; One-pot synthesis; β-Arabinofuranosylation; β-L-Araf-L-Hyp4; OLIGOSACCHARIDES; HYDROXYPROLINE; DONORS; MAJOR ALLERGEN; beta-Arabinofuranosylation; ONE-POT GLYCOSYLATION; MUGWORT POLLEN ALLERGEN; BIOSYNTHESIS; beta-L-Araf-L-Hyp; O-GLYCANS; ART V 1; STEREOSELECTIVE-SYNTHESIS; β-L-Araf-L-Hyp
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2018.02.006

We describe a β-L-arabinofuranosylation method by employing the 5-O-(2-pyridinecarbonyl)-L-arabinofuranosyl trichloroacetimidate 10 as a donor. This approach allows a wide range of acceptor substrates, especially amino acid acceptors, to be used. Stereoselective synthesis of β-(1,4)-L-arabinofuranosyl-(2S, 4R)-4-hydroxy-L-proline (β-L-Araf-L-Hyp4) and its dimer is achieved readily by this method. Both the stereoselectivities and yields of the reactions are excellent. To demonstrate the utility of this methodology, the preparation of a trisaccharide in a one-pot manner was carried out. [Display omitted] •A β-arabinofuranosylation method.•Selectivity by HAD effect.•Synthesis of β-L-Araf-Hyp and its dimer in high yields and stereoselectivities.