Diastereoselective desymmetric 1,2-cis-glycosylation of meso-diols via chirality transfer from a glycosyl donor

Masamichi Tanaka, Koji Sato, Ryoki Yoshida, Nobuya Nishi, Rikuto Oyamada, Kazuki Inaba, Daisuke Takahashi () and Kazunobu Toshima ()
Additional contact information
Masamichi Tanaka: Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi
Koji Sato: Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi
Ryoki Yoshida: Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi
Nobuya Nishi: Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi
Rikuto Oyamada: Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi
Kazuki Inaba: Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi
Daisuke Takahashi: Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi
Kazunobu Toshima: Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi

Nature Communications, 2020, vol. 11, issue 1, 1-10

Abstract: Abstract Chemical desymmetrization reactions of meso-diols are highly effective for the precise and efficient synthesis of chiral molecules. However, even though enzyme-catalyzed desymmetric glycosylations are frequently found in nature, there is no method for highly diastereoselective desymmetric chemical glycosylation of meso-diols. Herein, we report a highly diastereoselective desymmetric 1,2-cis-glycosylation of meso-diols found in myo-inositol 1,3,5-orthoesters using a boronic acid catalyst based on predictions of regioselectivity by density functional theory (DFT) calculations. The enantiotopic hydroxyl groups of the meso-diols are clearly differentiated by the stereochemistry at the C2 position of the glycosyl donor with excellent regioselectivities. In addition, the present method is successfully applied to the synthesis of core structures of phosphatidylinositolmannosides (PIMs) and glycosylphosphatidylinositol (GPI) anchors, and common β-mannoside structures of the LLBM-782 series of antibiotics.

Date: 2020
References: Add references at CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-020-16365-8 Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-16365-8

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/s41467-020-16365-8

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().