A pentacarbomethoxycyclopentadiene (PCCP) organic Brønsted acid catalyzed stereoselective glycosidation of N-pentenyl orthoesters (NPOE) of d-glucose and d-galactose, in conjunction with N-iodosuccinimide. (December 2022)

• Record Type: Journal Article
• Authors: Aswathy, Maniyamma; Abhijith, Balan; Lankalapalli, Ravi S.; Radhakrishnan, Kokkuvayil V.
• Is Part Of: Carbohydrate research. Volume 522(2022)
• Publication Date: 2022-12
• Subjects: Glycosidation -- Organic Brønsted acid -- PCCP -- N-Pentenyl orthoesters -- Stereoselectivity; PCCP pentacarbomethoxycyclopentadiene; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2022.108684
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: Herein, we report our preliminary results in utilizing the organic Brønsted acid, pentacarbomethoxycyclopentadiene (PCCP), for catalysing the glycosidation with n -pentenyl orthoesters (NPOE) of d -glucose and d -galactose in the presence of N -iodosuccinimide (NIS). Benzoyl and benzyl protection in d -glucosyl NPOEs led to 1, 2-trans glycosides, while acetyl protection in NPOE led to a mixture of 1, 2-cis and trans glycosides with >75% cis selectivity, and d -galactosyl NPOEs led to 1, 2-orthoesters. Substrate scope was demonstrated with acceptors of natural product relevance. This article highlights the prospect of utilizing the organic Brønsted acid, PCCP, for stereoselective glycosidation. Graphical abstract: Image 1 Highlights: A pentacarbomethoxycyclopentadiene (PCCP), organic Brønsted acid, catalyzed glycosidation. Stereoselective glycosidation of N -pentenyl orthoesters (NPOE) with PCCP catalyst in conjunction with N -iodosuccinimide. Benzoyl and benzyl protection in d -glucosyl NPOEs led to 1, 2-trans glycosides. Substrate scope was demonstrated with aglycones of natural product relevance.