EP0679159A1 - $g(a)-AMINONITRILES DERIVES D'UN SUCRE AMINE - Google Patents

$g(a)-AMINONITRILES DERIVES D'UN SUCRE AMINE

Info

Publication number
EP0679159A1
EP0679159A1 EP94906573A EP94906573A EP0679159A1 EP 0679159 A1 EP0679159 A1 EP 0679159A1 EP 94906573 A EP94906573 A EP 94906573A EP 94906573 A EP94906573 A EP 94906573A EP 0679159 A1 EP0679159 A1 EP 0679159A1
Authority
EP
European Patent Office
Prior art keywords
amino sugar
compound
amino
aldehyde
sugar
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP94906573A
Other languages
German (de)
English (en)
Inventor
Alison A. Fleming
Gurudas D. Sinai-Zingde
Meiylin F. Antezzo
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Akzo Nobel NV
Original Assignee
Akzo Nobel NV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Akzo Nobel NV filed Critical Akzo Nobel NV
Publication of EP0679159A1 publication Critical patent/EP0679159A1/fr
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/12—Acyclic radicals, not substituted by cyclic structures attached to a nitrogen atom of the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/16—Preparation of carboxylic acid nitriles by reaction of cyanides with lactones or compounds containing hydroxy groups or etherified or esterified hydroxy groups

Definitions

  • H. Kunz and co-workers have proposed the reaction of an O-pivaloyl-galactosylamine with aldehydes and a cyanide source to form the N-galactosyl ⁇ -amino nitriles (see Liebigs Ann. Chem. 1991, 649-654 and International Patent Application No. WO88/00592) .
  • the galactosylamine reagent by Kunz can be envisioned as a derivative of an "amino sugar" (which for purposes of this invention is defined as an amine-functionalized sugar molecule) where the anomeric oxygen has been replaced with a nitrogen atom and the hydroxyl groups have been protected.
  • This invention relates to the formation of an ⁇ -amino- nitrile compound by reaction of an amino sugar, a carbonyl compound, and a cyanide source.
  • amino sugar as used herein is intended to relate to sugar, or carbohydrate, molecules which contain one or more amino groups in place of the hydroxy moiety or moieties ordinarily contained as substituents thereon. It is within the contemplation of the present invention to cover both acyclic as well as cyclic sugar species. Monosaccharides, disaccharide, and polysaccharide-derived amino sugars can be utilized. Acyclic monosaccharides such as glucamine and fructamine are representative of amino sugars which can be used herein.
  • the amino sugar reagent used in the present process does not require protection of the hydroxyl groups contained therein, for example.
  • the carbonyl compound which is used herein as a second reagent is preferably a bisulfite addition product of an aldehyde having the structure RC(0)H, where R can be alkyl, aryl, alkylaryl, or arylalkyl. Preferably R is either straight chain or branched chain alkyl of from one to fourteen carbon atoms.
  • Some representative aldehydes which can be used include isobutyraldehyde, 2-ethylhexanal, and decanal. Ketones of the formula R-C(0)-R, with R being the same or different and defined as above can also be used.
  • the cyanide source is preferably an alkali metal cyanide, such as sodium cyanide.
  • the reaction of amino sugar, carbonyl compound, and cyanide source can be carried out in organic solvent, a mixed organic/aqueous solvent, or an all aqueous solvent medium.
  • the organic solvent if used, can be a water-miscible polar protic solvent (e.g., an alcohol), or a water-miscible polar aprotic solvent (e.g., tetrahydrofuran or dimethyl sulfoxide) .
  • Polar and non-polar solvents that are water immiscible e.g. , methylene chloride or toluene
  • the reaction temperature can vary widely (e.g., from about 0°C to the reflux temperature of the reaction medium, preferably 20°C to 60°C) . Stoichiometric amounts of amino sugar, carbonyl compound, and cyanide source are preferred.
  • the ⁇ -aminonitrile products derived from the process are intended as surfactants, chelants, or dispersants with the moiety derived from the amino sugar improving such properties as water solubility, biodegradability and chelation.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Biotechnology (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Toxicology (AREA)
  • Saccharide Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

On peut former un α-aminonitrile en faisant réagir un sucre aminé tel que du glucamine ou de glucosamine, un composé carbonylique tel qu'un produit d'addition de bisulfite d'aldéhyde et une source cyanurée telle qu'un cyanure de métal alcalin.
EP94906573A 1993-01-14 1994-01-10 $g(a)-AMINONITRILES DERIVES D'UN SUCRE AMINE Pending EP0679159A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US627293A 1993-01-14 1993-01-14
US6272 1993-01-14
PCT/US1994/000308 WO1994015941A1 (fr) 1993-01-14 1994-01-10 α-AMINONITRILES DERIVES D'UN SUCRE AMINE

Publications (1)

Publication Number Publication Date
EP0679159A1 true EP0679159A1 (fr) 1995-11-02

Family

ID=21720107

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94906573A Pending EP0679159A1 (fr) 1993-01-14 1994-01-10 $g(a)-AMINONITRILES DERIVES D'UN SUCRE AMINE

Country Status (2)

Country Link
EP (1) EP0679159A1 (fr)
WO (1) WO1994015941A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004089878A1 (fr) * 2003-04-02 2004-10-21 Tanabe Seiyaku Co., Ltd. Procede de production d'un compose alpha-aminonitrile optiquement actif
WO2013109523A1 (fr) * 2012-01-18 2013-07-25 Dow Corning Corporation Procédés de fabrication de copolymères de saccharide et de siloxane

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2164781A (en) * 1934-07-26 1939-07-04 Gen Aniline Works Inc Amino-carboxylic acids and a process of preparing them
US2443334A (en) * 1942-02-18 1948-06-15 Parke Davis & Co Manufacture of vitamin intermediates
US2833757A (en) * 1953-10-12 1958-05-06 Atlas Powder Co N-cyanoalkyl hexityl amines
GB808093A (en) * 1955-12-20 1959-01-28 Bayer Ag Therapeutically valuable calcium salts
DE3624376A1 (de) * 1986-07-18 1988-01-28 Horst Prof Dr Kunz Glycosylamine und deren n-alkyliden-derivate

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9415941A1 *

Also Published As

Publication number Publication date
WO1994015941A1 (fr) 1994-07-21

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