WO1988000592A1 - SYNTHESE DIASTEREOSELECTIVE DE STRECKER D'ACIDES AMINES alpha A PARTIR DE DERIVES DE GLYCOSYLAMINE - Google Patents

SYNTHESE DIASTEREOSELECTIVE DE STRECKER D'ACIDES AMINES alpha A PARTIR DE DERIVES DE GLYCOSYLAMINE Download PDF

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Publication number
WO1988000592A1
WO1988000592A1 PCT/EP1987/000371 EP8700371W WO8800592A1 WO 1988000592 A1 WO1988000592 A1 WO 1988000592A1 EP 8700371 W EP8700371 W EP 8700371W WO 8800592 A1 WO8800592 A1 WO 8800592A1
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WIPO (PCT)
Prior art keywords
compounds
formula
compounds according
radical
synthesis
Prior art date
Application number
PCT/EP1987/000371
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German (de)
English (en)
Inventor
Horst Kunz
Wilfried Sager
Waldemar Pfrenge
Mathias Decker
Original Assignee
Shell Agrar Gmbh & Co. Kg
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 Shell Agrar Gmbh & Co. Kg filed Critical Shell Agrar Gmbh & Co. Kg
Priority to JP50452687A priority Critical patent/JPH03501966A/ja
Publication of WO1988000592A1 publication Critical patent/WO1988000592A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms

Definitions

  • Dias teredm ere pure It can be isolated in a yield of approximately 65%.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des glycosylamines à O-acyl protégé, en particulier 2,3,4,6-tétra-O-pivaloyl-beta-D-galactopyranosylamine (1), leur préparation et leur utilisation pour la synthèse diastéréosélective d'acides aminés alpha. On peut obtenir par synthèse de Strecker avec des composés tels que (1) des rendements et des excédents élevés de diastéréomères, le sens de l'induction asymétrique pouvant être déterminé par le choix du solvant. Ce type de synthèse est particulièrement efficace lorsqu'il est effectué en présence d'acides de Lewis catalyseurs. En utilisant des amines telles que (1), on peut également obtenir des rendements élevés et une bonne diastéréosélectivité pendant des procédés de synthèse à quatre composantes selon Ugi facilités par des acides de Lewis.
PCT/EP1987/000371 1986-07-18 1987-07-10 SYNTHESE DIASTEREOSELECTIVE DE STRECKER D'ACIDES AMINES alpha A PARTIR DE DERIVES DE GLYCOSYLAMINE WO1988000592A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP50452687A JPH03501966A (ja) 1987-07-10 1987-07-10 グリコシルアミンとそのＮ‐アルキリデン誘導体；その製造法と特にα‐アミノ酸とその誘導体のジアステレオ選択合成におけるその使用

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19863624376 DE3624376A1 (de) 1986-07-18 1986-07-18 Glycosylamine und deren n-alkyliden-derivate
DEP3624376.0 1986-07-18

Publications (1)

Publication Number Publication Date
WO1988000592A1 true WO1988000592A1 (fr) 1988-01-28

Family

ID=6305504

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1987/000371 WO1988000592A1 (fr) 1986-07-18 1987-07-10 SYNTHESE DIASTEREOSELECTIVE DE STRECKER D'ACIDES AMINES alpha A PARTIR DE DERIVES DE GLYCOSYLAMINE

Country Status (3)

Country Link
EP (1) EP0274515A1 (fr)
DE (1) DE3624376A1 (fr)
WO (1) WO1988000592A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994015941A1 (fr) * 1993-01-14 1994-07-21 Akzo N.V. α-AMINONITRILES DERIVES D'UN SUCRE AMINE
FR2721612A1 (fr) * 1994-06-23 1995-12-29 Idm Nouveaux dérivés d'oligosides, leur procédé de préparation et leurs applications.
WO2003006474A2 (fr) * 2001-07-11 2003-01-23 Schering Aktiengesellschaft Procede de production de 1-o-glycosides peracyles
US6831164B2 (en) 2001-07-11 2004-12-14 Schering Aktiengesellschaft Process for the production of peracylated 1-0-glycosides
CN1300090C (zh) * 2005-03-02 2007-02-14 杭州师范学院 一种芳基乙酸的制备方法
US8967361B2 (en) 2013-02-27 2015-03-03 Outerwall Inc. Coin counting and sorting machines
US9022841B2 (en) 2013-05-08 2015-05-05 Outerwall Inc. Coin counting and/or sorting machines and associated systems and methods
US9036890B2 (en) 2012-06-05 2015-05-19 Outerwall Inc. Optical coin discrimination systems and methods for use with consumer-operated kiosks and the like
US9443367B2 (en) 2014-01-17 2016-09-13 Outerwall Inc. Digital image coin discrimination for use with consumer-operated kiosks and the like

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991017141A2 (fr) * 1990-04-26 1991-11-14 Schering Corporation Procede diastereoselectif de preparation d'acides amines a substitution n et derives
WO2000043352A1 (fr) * 1999-01-22 2000-07-27 Pharmacore, Inc. Methode permettant de synthetiser des composes de formule 1 et leurs derives

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
Angewandte Chemie, International Edition in English, Band 24, 1985, VCH Verlagsgesellschaft mbH, (Weinheim, DE), L.F. TIETZE et al.: "Synthesis of 1,4- Dihydropyridine Nucleosides by Photochemical Cycloaddition", seiten 127-128 siehe seite 128, verbindungen 3A-C *
Angewandte Chemie, International Edition in English, Band 26, Nr. 1987, VCH Verlagsgesellschaft mbH, (Weinheim, DE), H. KUNZ et al.: "Diasteroselective Strecker Synthesis of alfa-Aminonitriles on Carbohydrate Templates", seiten 557-559 siehe das ganze dokument *
CHEMICAL ABSTRACTS, Chemical Substance Index, Band 102, Teil 3, Januar-Juni 1985, (Columbus, Ohio, US), siehe seite 3471, beta-D-Glucopyranosylamine -,N-((4-Bromophenyl)Methylene)-2,3,4,6- Tetraacetate -,N-((4-Chlorophenyl)Methylene) -2,3,4,6- Tetraacetate -,N-((4-Methoxyphenyl)Methylene)-2,3,4,6- Tetraacetate -,N-((4-Nitrophenyl)methylene)-2,6,4,6- Tetraacetate -,N-(Phenylmethylene)-2,3,4,6-Tetraacetate & CHEMICAL ABSTRACTS, Band 102, Nr. 7, 18. Februar 1985, (Columbus, Ohio US), G. WESTPHAL et al.: "Studies on the Maillard Reaction. Part 12. Formation of a Bisgluco-Sylamine Derivative", siehe seite 487, Zusammenfassung Nr. 60884, & Nahrung 1984, vol. 82, no.8, pages 809-814 *
CHEMICAL ABSTRACTS, Ninth Colletctive Index, Bande 76-85, 1972-1976, Formulas, (Columbus, Ohio, US), siehe seite 11528, C21H24N2011 beta-D-Glucopyranosylamine, N-((3-Nitrophenyl)- Methylene)-2,3,4,6-Tetraacetate C21H24N2O12, beta-D-Glucopyranosylamine, N-((2-Hydroxy-5-Nitrophenyl)Methylene - 2,3,4,6-Tetraacetate und seite 11560, C21H25NO10, beta-D-Glucopyranosylamine, N-((2-Hydroxyphenyl) Methylene)-2,3,4,6-Tetraacetate -,N-((4-Hydroxyphenyl)Methylene)-2,3,4,6-Tetraacetate & Chemical Abstract, Band 83, Nr. 3, 21. Juli 1975, (Columbus, Ohio, US), S.H. DOSS et al.: "NMR Studies on the Effect of the Nitrogen Atom on the Anomeric Proton of beta-D-Glucopyranosides", siehe seiten 542-543, Zusammenfassung Nr. 28518n, & Rev. Roum. Chim. 1974, vol. 19, no. 11, pages 1767-1772 *
Chemische Berichte, Band 106, 1973, Verlag Chemie GmbH, (Weinheim, DE), K. WEINGES et al.: "Die Asymmetrische Strecker-Synthese von Aliphatischen alfa-Methyl-alfa-Aminosauren", seiten 2291-2297 siehe seite 2291, Zusammenfassung *
Journal of the Chemical Society, Chemical Communications, Nr. 1, 7. Januar 1976, G. MacKENZIE et al.: "Synthesis of Analogues of 5-Aminoimidazole Ribonucleotides and Their Effects as Inhibitors and Substrates of the Enzymes, Phosphoribosylaminoimidazole Carboxylase and Phosphoribosylaminoimidazole-Succinocarboxamide Synthetase Involved in the Biosynthesis of Purine Nucleotides de Novo", seiten 453-455 siehe seite 454, Verbindung Ib *
The Journal of Organic Chemistry, Band 43, Nr. 10, 12. Mai 1978, American Chemical Society, (US). R.J.M. NOLTE et al.: "Poly(Iminomethylenes). 6. Synthesis and Polymerization of alfa- and beta-D-Glucopyranosyl Isocyanide" seiten 1972-1975 siehe seite 1972, Schema 1, Verbindung 5a *
The Journal of Organic Chemistry, Band 49, Nr. 10, 18. Mai 1984, American Chemical Society, (US), S.-Y. CHEN et al.: "Total Synthesis of Two Furanomycin Steroisomers" seiten 1769-1772 siehe seite 1770, spalte 1, zeilen 85-35 *

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994015941A1 (fr) * 1993-01-14 1994-07-21 Akzo N.V. α-AMINONITRILES DERIVES D'UN SUCRE AMINE
FR2721612A1 (fr) * 1994-06-23 1995-12-29 Idm Nouveaux dérivés d'oligosides, leur procédé de préparation et leurs applications.
WO1996000229A1 (fr) * 1994-06-23 1996-01-04 I.D.M. Immuno-Designed Molecules Nouveaux derives d'oligosides, leur procede de preparation et leurs applications
US6251858B1 (en) 1994-06-23 2001-06-26 I.D.M. Immuno-Designed Molecules Derivatives of oligosides, their process of preparation and their applications
US6831164B2 (en) 2001-07-11 2004-12-14 Schering Aktiengesellschaft Process for the production of peracylated 1-0-glycosides
WO2003006474A3 (fr) * 2001-07-11 2003-05-01 Schering Ag Procede de production de 1-o-glycosides peracyles
WO2003006474A2 (fr) * 2001-07-11 2003-01-23 Schering Aktiengesellschaft Procede de production de 1-o-glycosides peracyles
CN1300090C (zh) * 2005-03-02 2007-02-14 杭州师范学院 一种芳基乙酸的制备方法
US9036890B2 (en) 2012-06-05 2015-05-19 Outerwall Inc. Optical coin discrimination systems and methods for use with consumer-operated kiosks and the like
US9594982B2 (en) 2012-06-05 2017-03-14 Coinstar, Llc Optical coin discrimination systems and methods for use with consumer-operated kiosks and the like
US8967361B2 (en) 2013-02-27 2015-03-03 Outerwall Inc. Coin counting and sorting machines
US9022841B2 (en) 2013-05-08 2015-05-05 Outerwall Inc. Coin counting and/or sorting machines and associated systems and methods
US9443367B2 (en) 2014-01-17 2016-09-13 Outerwall Inc. Digital image coin discrimination for use with consumer-operated kiosks and the like

Also Published As

Publication number Publication date
DE3624376A1 (de) 1988-01-28
EP0274515A1 (fr) 1988-07-20

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