US 5268461

US5268461A — Alkylated oligosaccharides and acetyl derivatives of the same

Bibliographic data (from the supplied source): Application US07/834,305; priority date 1990‑06‑27; filing date 1991‑06‑27; granted/publication date 1993‑12‑07. Original assignee Dainippon Ink and Chemicals Co Ltd; current assignee listed as DIC Corp. Inventors: Tadao Shoji, Nahoko Takahashi, Koichiro Adachi, Naoya Ikushima, Kaname Katsuraya, Toshiyuki Uryu, Takashi Yoshida. Legal status shown as "Expired – Fee Related," with anticipated expiration 2011‑06‑27. Classifications: C07H15/00, C07H15/02, C07H15/04, C07H3/00, C07H3/06.

Purpose: The patent concerns alkylated oligosaccharides and their acetyl derivatives, described as useful raw materials for low-toxicity surfactants or medicines. The compounds are said to act as surfactants because they combine hydrophilic sugar-chain moieties with hydrophobic alkyl groups, and to offer improved absorption relative to conventional polysaccharides owing to lower molecular weight.

Plain-language scope: The claimed subject matter, as described, covers compounds in which the hydrogen of the hydroxy group at the 1-position of the terminal sugar moiety of certain oligosaccharides is replaced by a linear or branched alkyl group. The oligosaccharide backbones are (a) oligosaccharides in which glucose moieties are β(1→4)-glycoside-linked, or (b) oligosaccharides in which galactose is β(1→4)-linked at the 4-position of the galactose moiety of lactose, with galactose moieties β(1→4)-linked in succession to the newly formed terminal galactose moieties. Alkyl groups have linear or branched chains of 1 to 22 carbon atoms, and the alkyl group is inserted at the anomer position. Acetyl derivatives, including compounds in which only the 2-positional hydroxy group adjacent to the alkyl-ether linkage is selectively deacetylated, are also described. The production method acetylates an oligosaccharide and reacts the acetylated product with an alcohol using a heteropolyacid (or Lewis acid) as reacting agent. Example compounds include n-dodecyl, n-heptyl, n-decyl and n-octadecyl galactopyranosyl-galactopyranosyl-glucopyranosides.

Not established by this excerpt: The excerpt is partial and omits the full claims, detailed examples, and any issued claim language. It does not establish claim scope as granted, validity, enforceability, litigation history, ownership transfers beyond the listed reassignment, or the content of the cited prior-art documents. No completeness of the compound list is warranted.

Source: https://patents.google.com/patent/[US5268461](/patent/US5268461)/en