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1. WO1996004291 - SYNTHESIS OF 4-ALKOXY-N-ACETYLNEURAMINIC ACID

Publication Number WO/1996/004291
Publication Date 15.02.1996
International Application No. PCT/US1995/009223
International Filing Date 21.07.1995
Chapter 2 Demand Filed 06.02.1996
IPC
C07H 15/04 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
15Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
02Acyclic radicals, not substituted by cyclic structures
04attached to an oxygen atom of a saccharide radical
CPC
C07H 15/04
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
15Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
02Acyclic radicals, not substituted by cyclic structures
04attached to an oxygen atom of the saccharide radical
Applicants
  • OKLAHOMA MEDICAL RESEARCH FOUNDATION [US/US]; 825 Northeast 13th Street Oklahoma City, OK 73104, US
Inventors
  • LIAV, Avraham; US
  • HARDGRAVE, Ragen, F.; US
  • BLYSTONE, Sheri; US
  • TURNER, Gregory, A.; US
Agents
  • SAMPLES, Kenneth, H. ; Fitch, Even, Tabin & Flannery Room 900 135 South LaSalle Street Chicago, IL 60603, US
Priority Data
08/286,57305.08.1994US
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) SYNTHESIS OF 4-ALKOXY-N-ACETYLNEURAMINIC ACID
(FR) SYNTHESE DE L'ACIDE 4-ALCOXY-N-ACETYLNEURAMINIQUE
Abstract
(EN)
This invention relates to an improved process for the synthesis of 4-alkoxy-N-acetylneuraminic acids. According to the process of the invention, N-acetylneuraminic acid is first alkylated at C-1 and C-2, and then the vicinal hydroxyl groups at C-8 and C-9 are protected through the formation of a ketal. The resulting protected alkyl ester alkyl ketoside is then alkylated at the C-4 position whereby the hydrogen of the C-4 hydroxyl group is replaced with an alkyl group to form an alkoxy group. Deprotection is accomplished through the removal of the ketal group at C-8 and C-9 and removal of the alkyl groups at C-1 and C-2, thereby producing the 4-alkoxy-N-acetylneuraminic acid.
(FR)
Cette invention se rapporte à un procédé de synthèse amélioré des acides 4-alcoxy-acétylneuraminiques. Selon le procédé de l'invention, l'acide N-acétylneuraminique est d'abord alkylé aux positions C-1 et C-2, puis les groupes hydroxyle voisins aux positions C-8 et C-9 sont protégés par la formation d'un cétal. L'alkyle ester alkyle cétoside protégé obtenu est ensuite alkylé à la position C-4, l'hydrogène du groupe hydroxyle en C-4 étant remplacé par un groupe alkyle pour former un groupe alcoxy. La déprotection s'effectue par le retrait du groupe cétal aux positions C-8 et C-9 et le retrait des groupes alkyle aux positions C-1 et C-2, ce qui permet d'obtenir l'acide 4-alcoxy-N-acétylneuraminique.
Also published as
KR1019970700744
NO19970462
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