AR060392A1 - Procesos para la sintesis quimica de lipoquitooligosacaridos, intermediarios de esos procesos y composiciones que los contienen. - Google Patents

Procesos para la sintesis quimica de lipoquitooligosacaridos, intermediarios de esos procesos y composiciones que los contienen.

Info

Publication number
AR060392A1
AR060392A1 ARP070101488A ARP070101488A AR060392A1 AR 060392 A1 AR060392 A1 AR 060392A1 AR P070101488 A ARP070101488 A AR P070101488A AR P070101488 A ARP070101488 A AR P070101488A AR 060392 A1 AR060392 A1 AR 060392A1
Authority
AR
Argentina
Prior art keywords
groups
mixture
product
processes
mono
Prior art date
Application number
ARP070101488A
Other languages
English (en)
Inventor
Sabesan Subramaniam
Original Assignee
Du Pont
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 Du Pont filed Critical Du Pont
Publication of AR060392A1 publication Critical patent/AR060392A1/es

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
    • 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
    • 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
    • C07H13/06—Fatty acids
    • 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
    • C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical

Landscapes

  • 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)
  • Crystallography & Structural Chemistry (AREA)
  • Saccharide Compounds (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Cultivation Of Plants (AREA)
  • Pretreatment Of Seeds And Plants (AREA)

Abstract

Procesos para la síntesis de lipoquitooligosacáridos. Se prepara un precursor de oligoglucosamina totalmente acilado y se hace reaccionar con un monomero de glucosamina que tiene un grupo ftaloilo protector de aminas. Con la eliminacion del grupo ftaloilo, se puede agregar un ácido graso a la unidad de glucosamina terminal, formando un Iipoquitooligosacárido. Los procesos se pueden adaptar para usarse a escala comercial. Reivindicacion 1: Un proceso para sintetizar un compuesto Iipoquitooligosacárido que tiene la estructura A en donde los grupos individuales R1, R2 y R3 se seleccionan independientemente entre H y grupos alquilo, arilo, aralquilo, mono, di o polialquenilo, mono, di o polialquinilo C1-20; R4 se selecciona entre un monosacárido, sulfato y fosfato; y n es entre 0 y aproximadamente 20; caracterizado porque comprende: a) combinar un compuesto de estructura C en donde R1 se selecciona entre H, grupos alquilo, arilo y aralquilo C1-20, con un compuesto de estructura B donde los grupos individuales R1 y R2 se seleccionan independientemente entre H y grupos alquilo, arilo y aralquilo C1-20; R4 se selecciona entre un monosacárido, un sulfato y un fosfato; y n es entre 0 y aproximadamente 19; en un solvente aprotico y agitando la solucion a una temperatura entre aproximadamente de 0°C y aproximadamente de -78°C para formar una primera mezcla; b) agregar a la mezcla de a) un primer agente activante que se selecciona entre N-haloimidas para formar una segunda mezcla; c) agregar un segundo agente activante que se selecciona entre ácidos perfluoroalquilsulfonicos, y opcionalmente agregar un reactivo que se selecciona entre sulfonatos de metilperfluoroalquilos a la segunda mezcla para formar una tercera mezcla; d) hacer reaccionar la tercera mezcla a una temperatura de entre aproximadamente de 0°C y aproximadamente de -78°C para formar un producto que comprende grupos ésteres y un grupo N-ftalimido; e) aislar el producto de d); f) eliminar los grupos ésteres y el grupo N-ftalimido del producto aislado de e) con lo que se forma un producto de-esterificado y des-N-ftalimidado; g) aislar el producto de f); h) hacer reaccionar en forma selectiva el grupo amino de la unidad de azucar terminal del producto aislado de g) con un ácido o un halogenuro de ácido de formula R1COX: en donde X = OH o un halogeno, para los ácidos y los halogenuros de ácidos, respectivamente, y R1 se selecciona entre H, grupos alquilo, arilo, aralquilo, mono, di o polialquenilo, mono, di o polialquinilo C1-20 para formar un lipoquitooligosacárido; y i) aislar el lipoquitooligosacárido.
ARP070101488A 2006-04-07 2007-04-09 Procesos para la sintesis quimica de lipoquitooligosacaridos, intermediarios de esos procesos y composiciones que los contienen. AR060392A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US79042906P 2006-04-07 2006-04-07

Publications (1)

Publication Number Publication Date
AR060392A1 true AR060392A1 (es) 2008-06-11

Family

ID=38521085

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP070101488A AR060392A1 (es) 2006-04-07 2007-04-09 Procesos para la sintesis quimica de lipoquitooligosacaridos, intermediarios de esos procesos y composiciones que los contienen.

Country Status (9)

Country Link
US (4) US20070238872A1 (es)
EP (3) EP2348027B1 (es)
JP (1) JP2009533345A (es)
KR (1) KR20090023563A (es)
CN (1) CN101421287A (es)
AR (1) AR060392A1 (es)
AU (1) AU2007235408A1 (es)
CA (1) CA2644172A1 (es)
WO (1) WO2007117500A2 (es)

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Also Published As

Publication number Publication date
EP2348027A1 (en) 2011-07-27
JP2009533345A (ja) 2009-09-17
US9090644B2 (en) 2015-07-28
US8049002B2 (en) 2011-11-01
KR20090023563A (ko) 2009-03-05
EP2010552B1 (en) 2011-07-06
EP2348027B1 (en) 2013-10-23
AU2007235408A1 (en) 2007-10-18
CN101421287A (zh) 2009-04-29
EP2010552A2 (en) 2009-01-07
EP2348028B1 (en) 2012-08-22
CA2644172A1 (en) 2007-10-18
WO2007117500A3 (en) 2008-04-03
EP2348028A1 (en) 2011-07-27
US20120004401A1 (en) 2012-01-05
US20070238872A1 (en) 2007-10-11
US20090292115A1 (en) 2009-11-26
US20140303361A1 (en) 2014-10-09
WO2007117500A2 (en) 2007-10-18

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