Synthesis and Biological Evaluation of O-Methylated Glycolipids Related to PGLs via Direct Stereoselective Glycosidation and Sequential Suzuki–Miyaura Coupling using Boracyclane

Ko Sato, Zakaria Omahdi, Kensuke Shibata, Koh Hei Sonoda, Sho Yamasaki, Hiroshi Tanaka

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Synthesis of O-methylated glycolipids via direct stereoselective glycosidation whose sugar moieties are related to those in phenolic glycolipids (PGLs) is reported. Treatment of 2-O-methyl-rhamnosyl imidates with I2 and nBu4NOTf resulted in their activation under low temperature and provided the α-rhamnosides with excellent α-selectivity. nBu4NOTf enhanced the electorophilicity of iodine. This methodology improved the efficiency of the synthesis of both PGL-1 and PGL-tb1 sugars. The process involved the formation of 2-O-naphthylmethyl-α-rhamnoside and 2-O-methyl-α-fucoside. Sequential Suzuki–Miyaura coupling using synthetic glycosides, boracyclane, and aryl bromides provided glycolipids related to PGL sugars, and was accomplished with a one-pot process. Finally, we elucidated the immunosuppressive activities of all these synthetic compounds and found that a phenyl 3-O-α-rhamnosyl-2-O-methyl-α-rhamnoside possessing a 6-(2-naphthyl)hexyl group exhibited the strongest inhibitory effect.

Original languageEnglish
Pages (from-to)16374-16379
Number of pages6
JournalChemistry - A European Journal
Volume23
Issue number64
DOIs
Publication statusPublished - Nov 16 2017

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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