SnCl2‐Catalyzed Acetalation/Selective Benzoylation Sequence for the Synthesis of Orthogonally Protected Glycosyl Acceptors

• Published in: European journal of organic chemistry Vol. 2022; no. 33
• Main Authors: Lv, Jian, Liu, Chun‐Yang, Guo, Yang‐Fan, Feng, Guang‐Jing, Dong, Hai
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 06.09.2022; Wiley Subscription Services, Inc
• Subjects: Acetalation; Antigens; Benzoylation; Blood groups; Chemistry; Chemistry, Organic; Galactosides; Glucosides; Glycosyl acceptor; One-pot; Physical Sciences; Science & Technology; Selective benzoylation; SnCl2-catalyzed; Tin chloride; ACID; OLIGOSACCHARIDES; Selective benzoylation; ONE-POT SYNTHESIS; ACETYLATION; CONVENIENT METHOD; One-pot; Glycosyl acceptor; CATALYST; Acetalation; SnCl2-catalyzed; FUNCTIONALIZATION; BENZYLIDENE ACETALS; GENERATION; EFFICIENT
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.202101565

Based on SnCl2‐catalyzed acetalation and selective benzoylation, a one‐pot strategy to efficiently synthesize orthogonally protected glycosyl acceptors with 2‐OH/3‐OH was developed. Consequently, 2‐OBz or 3‐OBz 4,6‐O‐benzylidene galactosides and glucosides were efficiently prepared in moderate to high yields starting from free galactosides and glucosides, and were used as valuable glycosyl acceptors for the synthesis of blood group antigens O and B analogues in this study. Based on SnCl2‐catalyzed acetalation and selective benzoylation, a one‐pot strategy to efficiently synthesize orthogonally protected glycosyl acceptors with 2‐OH/3‐OH was developed.