Synthesis of hexopyranosyl pyrimidine homonucleosides. Issue 3 (1st February 2021)

• Record Type: Journal Article
• Authors: Verma, Vineet; Maikhuri, Vipin K.; Khatri, Vinod; Singh, Ankita; Prasad, Ashok K.
• Is Part Of: Synthetic communications. Volume 51:Issue 3(2021)
• Page Start: 446
• Page End: 452
• Publication Date: 2021-02-01
• Subjects: 2, 6-Anhydro-heptitols -- hexopyranosyl double-headed homonucleosides -- hexopyranosyl homonucleosides -- hexopyranosyl pyrimidine homonucleosides; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2020.1836224
• Languages: English
• ISSNs: 0039-7911

Abstract

Abstract: A simple and convenient methodology has been developed for the synthesis of novel hexopyranosyl pyrimidine homonucleosides and hexopyranosyl double-headed pyrimidine homonucleosides from the corresponding native sugars, d -glucose and d -mannose. Thus, hexose sugars were converted to 2, 6-anhydro-3, 4, 5, 7-tetra- O -benzyl-heptitols and 2, 6-anhydro-3, 4, 5-tri- O -benzyl-heptitols by recently developed procedure of Khatri et al. Further, mono- and di-hydroxy 2, 6-anhydro-heptitols were converted to their corresponding mono- and di-tosylated derivatives, which were then translated into hexopyranosyl homonucleosides and double-headed homonucleosides by reaction with uracil and thymine in 40–50 and 27–73% overall yields from tetra- and tri- O -benzylated anhydro-heptitols. Graphical Abstract: