Bioscience, Biotechnology, and Biochemistry
Online ISSN : 1347-6947
Print ISSN : 0916-8451
Organic Chemistry Regular Papers
Synthesis of a Spacer-Linked Derivative of Heptopyranosyl(α1-3)heptopyranose Expressed in Lipooligosaccharide and Lipopolysaccharide
Ryohei YAMASAKIKaori NAGAHARAKatsuya KISHIMOTOAkihiko TAKAJYO
著者情報
ジャーナル フリー

2012 年 76 巻 4 号 p. 772-777

詳細
抄録
Glycosylation of penta-O-acetyl heptopyranosyl trichloroacetimidate with the 3-OH acceptor, methyl 2-O-benzyl-4,6-O-benzylidene-7,8-dideoxy-α-D-manno-oct-7-enopyranoside, gave the desired α1-3-linked disaccharide in a 94% yield. The oct-enopyranoside moiety of the disaccharide was converted to the heptoside by oxidative cleavage with osmium tetroxide/NaIO4 and subsequent reduction with NaBH4. The resulting α1-3-linked heptose disaccharide was converted to a tricholoroacetaimidate derivative containing a benzoyl group at C-2. This donor was glycosylated with 2-(carbobenzoxyamino)-1-ethanol to give an α spacer-linked disaccharide derivative in a 90% yield. Zemplén deacylation of the derivative and subsequent hydrogenolysis gave a 2-aminoethyl glycoside of heptopyranosyl(α1-3)heptopyranose.
著者関連情報

この記事は最新の被引用情報を取得できません。

© 2012 by Japan Society for Bioscience, Biotechnology, and Agrochemistry
前の記事 次の記事
feedback
Top