Sialic acid analogs
US-9221858-B2 · Dec 29, 2015 · US
US10100074B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-10100074-B2 |
| Application number | US-201514975537-A |
| Country | US |
| Kind code | B2 |
| Filing date | Dec 18, 2015 |
| Priority date | Jun 19, 2013 |
| Publication date | Oct 16, 2018 |
| Grant date | Oct 16, 2018 |
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The present invention provides novel, regioselectively-acylated oligosaccharide compounds and methods for preparing them. In another aspect, the. invention provides a method for preparing a selectively-acylated oligosaccharide. The method includes forming a reaction mixture containing a protected oligosaccharide and an acylating agent. The protected oligosaccharide includes at least three hydroxyl moieties and each hydroxyl moiety is protected with a silyl protecting group. The reaction mixture is formed under conditions sufficient to selectively replace at least one silyl protecting group with a —C(0)-C1_6 alkyl group, and the selectively-acylated oligosaccharide comprises at least one —C(0)-C1_6 alkyl group and at least one silyl protecting group.
Opening claim text (preview).
What is claimed is: 1. A selectively-acylated oligosaccharide selected from the group consisting of: wherein each TMS is Si(Me) 3 and each Ac is C(O)Me. 2. A method for preparing a selectively-acylated oligosaccharide according to claim 1 , the method comprising forming a reaction mixture comprising a per-O-trimethylsilyl oligosaccharide and an acylating agent, wherein the acylating agent is acetic anhydride, and the reaction mixture is formed under conditions sufficient to selectively replace at least one trimethylsilyl group with a —C(O)Me group, thereby preparing the selectively-acylated oligosaccharide.
Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12 (esters with inorganic acids C07H11/00) · CPC title
Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups · CPC title
having the esterifying carboxyl radicals attached to acyclic carbon atoms · CPC title
Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages · CPC title
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