WO1994015941A1 - α-AMINONITRILES DERIVES D'UN SUCRE AMINE - Google Patents

α-AMINONITRILES DERIVES D'UN SUCRE AMINE Download PDF

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Publication number
WO1994015941A1
WO1994015941A1 PCT/US1994/000308 US9400308W WO9415941A1 WO 1994015941 A1 WO1994015941 A1 WO 1994015941A1 US 9400308 W US9400308 W US 9400308W WO 9415941 A1 WO9415941 A1 WO 9415941A1
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WO
WIPO (PCT)
Prior art keywords
amino sugar
compound
amino
aldehyde
sugar
Prior art date
Application number
PCT/US1994/000308
Other languages
English (en)
Inventor
Alison A. Fleming
Gurudas D. Sinai-Zingde
Meiylin F. Antezzo
Original Assignee
Akzo N.V.
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 N.V. filed Critical Akzo N.V.
Priority to EP94906573A priority Critical patent/EP0679159A1/fr
Publication of WO1994015941A1 publication Critical patent/WO1994015941A1/fr

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Saccharide Compounds (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.
PCT/US1994/000308 1993-01-14 1994-01-10 α-AMINONITRILES DERIVES D'UN SUCRE AMINE WO1994015941A1 (fr)

Priority Applications (1)

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

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US627293A 1993-01-14 1993-01-14
US08/006,272 1993-01-14

Publications (1)

Publication Number Publication Date
WO1994015941A1 true WO1994015941A1 (fr) 1994-07-21

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Family Applications (1)

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

Country Status (2)

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

Cited By (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
KR20140116928A (ko) * 2012-01-18 2014-10-06 다우 코닝 코포레이션 사카라이드 실록산 공중합체를 제조하는 방법

Citations (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
WO1988000592A1 (fr) * 1986-07-18 1988-01-28 Shell Agrar Gmbh & Co. Kg SYNTHESE DIASTEREOSELECTIVE DE STRECKER D'ACIDES AMINES alpha A PARTIR DE DERIVES DE GLYCOSYLAMINE

Patent Citations (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
WO1988000592A1 (fr) * 1986-07-18 1988-01-28 Shell Agrar Gmbh & Co. Kg SYNTHESE DIASTEREOSELECTIVE DE STRECKER D'ACIDES AMINES alpha A PARTIR DE DERIVES DE GLYCOSYLAMINE

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
Aldrich Chemical Co., "Aldrich Catalog Handbook of Fine Chemicals", published 1984 by Aldrich Chemical Company, Inc. (Milwaukee, WI), page 573, entire document. *
CHEM. ABSTR. Volume 53, issued 1959, S. PEARSON, Abstract of "Calcium Salts", Abstr. No. 10671c; & GB,A,808093. *
Chem. Pharm. Bull., Volume 16, No. 8, issued August 1968, SUZUE et al., "Studies on Hepatic Agents. I. Synthesis of Aminoacyl (and Hydroxyacyl) Aminoacetonitriles", pages 1417-1432, entire document. *
Russ. Chem. Rev. (Uspekhi Khimii), Volume 58, No. 2, issued 1989, SHAFRAN et al., "Synthesis and Properties of a-Aminonitriles", pp. 146-162, (orig. citation, Volume 58, No. 2, pages 250-274), entire document. *
Tetrahedron Letters, Volume 29, No. 35, issued 1988 (Gr. Britain), KUNZ et al. (II), "Reversal of Asymmetric Induction in Stereoselective Strecker Synthesis on Galactosyl Amine as the Chiral Matrix", pages 4397-4400, entire document. *

Cited By (3)

* 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
KR20140116928A (ko) * 2012-01-18 2014-10-06 다우 코닝 코포레이션 사카라이드 실록산 공중합체를 제조하는 방법
KR102043605B1 (ko) * 2012-01-18 2019-11-12 다우 실리콘즈 코포레이션 사카라이드 실록산 공중합체를 제조하는 방법

Also Published As

Publication number Publication date
EP0679159A1 (fr) 1995-11-02

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