Divergent Synthesis of 3-Deoxy-d-manno-oct-2-ulosonic Acid (Kdo) Glycosides Containing α-(2→4)-Linked Kdo-Kdo Unit.

A convenient and divergent approach was developed to prepare diverse bacterial 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo) oligosaccharides containing a Kdo-α-(2→4)-Kdo fragment. The orthogonal protected α-(2→4) linked Kdo-Kdo disaccharide 3, serving as a common precursor, was divergently transformed into the corresponding 8-, 8'-, and 4'-hydroxy disaccharides 5, 7, and 14, respectively. Then, these alcohols were glycosylated, respectively, with the 5,7-O-di-tert-butylsilylene (DTBS) protected Kdo thioglycoside donors 1 or 2 in an α-stereoselective and high-yielding manner to afford a range of Kdo oligosaccharides. Finally, removal of all protecting groups of the newly formed glycosides resulted in the desired free Kdo oligomer.

• Publication year

  2019

• Venue

  Chemistry - An Asian Journal

• Publication date

  2019-02-01

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1002/asia.201801779PMID 30516348
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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