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    PROCESS FOR PRODUCING 2'-O-FUCOSYLLACTOSE
    1.
    发明申请
    PROCESS FOR PRODUCING 2'-O-FUCOSYLLACTOSE 有权

    公开(公告)号：US20210130384A1

    公开(公告)日：2021-05-06

    申请号：US16074168

    申请日：2017-02-02

    Applicant: BASF SE

    Inventor： MICHAEL PUHL ,  Wolfgfang SIEGEL ,  Stephanie RENZ ,  Andreas WÖLFERT

    IPC: C07H1/06 ,  C07H15/18 ,  C07H3/06

    Abstract: The present invention relates to a method for preparing 2′-O-fucosyllactose, the intermediates obtainable by this method and the use of these intermediates. The preparation comprises the reaction of a protected fucose of the general formula (I) with a tri(C1-C6-alkyl)silyl iodide to give a protected 1-iodofucose followed by the reaction of the protected 1-iodofucose with a compound of the general formula (II), in the presence of at least one base and deprotecting the resulting coupling product to afford 2′-O-fucosyllactose. In this context, the variables are each defined as follows: Ra and Rb are the same or different and are —C(═O)—C1-C6-alkyl, or —C(═O)-phenyl, wherein said phenyl is unsubstituted or optionally has 1 to 5 substituents, or Ra and Rb together are a radical —(C═O)— or a substituted methylene radical —C(RdRe)—, Rc is a radical RSi or is benzyl, wherein said benzyl is unsubstituted or optionally has 1, 2 or 3 substituents, RSi is a radical of the formula SiRfRgRh, where Rf, Rg and Rh are the same or different and are C1-C8-alkyl for example, R1 is a radical —C(═O)—R11 or a radical SiR12R13R14 R2 are the same or different and are C1-C8-alkyl for example; R3 are the same or different and are for example C1-C8-alkyl or both radicals R3 together form a linear C1-C4-alkenyl, which is unsubstituted or has 1 to 6 methyl groups as substituents.

    METHOD FOR PREPARING 2'-O-FUCOSYLLACTOSE
    2.
    发明申请
    METHOD FOR PREPARING 2'-O-FUCOSYLLACTOSE 审中-公开

    公开(公告)号：US20190100547A1

    公开(公告)日：2019-04-04

    申请号：US16082581

    申请日：2017-03-08

    Applicant: BASF SE

    Inventor： MICHAEL PUHL ,  Stephanie RENZ ,  Andreas WOELFERT

    IPC: C07H3/08 ,  C07H1/00

    Abstract: The present invention relates to a method for preparing 2′-O-fucosyllactose and to the protected fucosyl donor of the formula (I) used in this method. The method comprises reacting the fucose derivative of the formula (I) below with the compound of the general formula (II), in the presence of an activating reagent. In the formulae (I) and (II), the variables are each defined as follows: X is Br or a S-bound radical, namely —SCN, —S(O)n—RX1or —S—RX2, wherein RX1 preferably is an optionally substituted phenyl, and RX2 preferably is C1-C4-alkyl, 2-oxazolin-2-yl, 2-thiazolin-2-yl, benzoxazol-2-yl, benzothiazol-2-yl or pyridin-2-yl; RSi are the same or different and are radicals of the formula SiRaRbRc, wherein Ra, Rb and Rc preferably are each methyl; R1 is a C(=O)—R11 radical or an SiR12R13R14 radical, wherein R11 is preferably methyl, phenyl or tert-butyl, and R12, R13 and R14 preferably are each methyl; R2 are the same or different and are C1-C8-alkyl or together form a linear C3-C6-alkanediyl, which is unsubstituted or has 1 to 6 methyl groups as substituents; R3 are the same or different and are C1-C8-alkyl or together form a linear C1-C4-alkanediyl, which is unsubstituted or has 1 to 6 methyl groups as substituents.

    METHOD FOR PREPARING 2'-O-FUCOSYLLACTOSE
    3.
    发明申请
    METHOD FOR PREPARING 2'-O-FUCOSYLLACTOSE 审中-公开

    公开(公告)号：US20180230176A1

    公开(公告)日：2018-08-16

    申请号：US15510268

    申请日：2015-09-11

    Applicant: BASF SE

    Inventor： MICHAEL PUHL ,  Klaus DITRICH ,  Andreas KELLER ,  Pepa DIMITROVA ,  Melanie WEINGARTEN ,  Wolfgang SIEGEL

    IPC: C07H15/26 ,  C07H3/06 ,  C07H1/00 ,  A23L33/10

    CPC classification number: C07H15/26 ,  A23L33/10 ,  A23V2002/00 ,  C07H1/00 ,  C07H3/06

    Abstract: The present invention relates to a method for preparing 2′-O-fucosyllactose, the 2′-O-fucosyllactose obtainable by this method and the use thereof. The method comprises reacting the persilylated, protected fucose derivatives of the formula (I) below, with at least one tri(C1-C6-alkyl)silyl iodide and subsequently reacting the product thus obtained with the compound of the general formula (II), in the presence of a base. In the formulae (I) and (II), the variables are each defined as follows: RSi are the same or different and are a residue of the formula SiRaRbRc; R1 is a C(═O)—R11 residue or an SiR12R13R14 residue, R2 are the same or different and are C1-C8-alkyl or together form a linear C3-C6-alkanediyl, which is unsubstituted or has 1 to 6 methyl groups as substituents; R3 are the same or different and are C1-C8-alkyl or together form a linear C1-C4-alkanediyl, which is unsubstituted or has 1 to 6 methyl groups as substituents.

    métodos para preparar 2?-o-fucosil-lactose e produtos alimentícios, composto, e, uso de um dos compostos
    6.
    发明专利
    métodos para preparar 2?-o-fucosil-lactose e produtos alimentícios, composto, e, uso de um dos compostos 未知

    公开(公告)号：BR112018015833A2

    公开(公告)日：2018-12-26

    申请号：BR112018015833

    申请日：2017-02-02

    Applicant: BASF SE

    Inventor： ANDREAS WOELFERT ,  MICHAEL PUHL ,  STEPHANIE RENZ ,  WOLFGANG SIEGEL

    IPC: A23C9/20 ,  A23L33/00 ,  C07H1/00 ,  C07H3/06 ,  C07H15/18 ,  C07H23/00

    Abstract: a presente invenção refere-se a um processo para produzir 2?-o-fucosil-lactose, aos intermediários obteníveis por esse processo e ao uso desses intermediários. a produção compreende a reação de uma fucose protegida da fórmula geral (i) com um iodeto de tri(c1-c6-alquil)silila para gerar uma 1-iodofucose protegida seguida pela reação da 1-iodofucose protegida com um composto da fórmula geral (ii), na presença de pelo menos uma base e desproteção do produto de acoplamento obtido para obter 2?-o-fucosil-lactose. as variáveis são definidas da seguinte forma: ra e rb são idênticos ou diferentes e representam -c(=o)-c1-c6-alquila ou -c(=o)-fenila, em que a fenila é não substituída ou compreende opcionalmente 1 a 5 substituintes, ou ra e rb representam, em conjunto, um radical (c=o) ou um radical metileno substituído c(rdre) , rc representa um radical rsi ou benzila, em que a benzila é não substituída ou porta opcionalmente 1, 2 ou 3 substituintes, rsi representa um radical da fórmula sirfrgrh, em que rf, rg e rh são idênticos ou diferentes e representam, por exemplo, c1 c8 alquila, r1 representa um radical -c(=o)-r11 ou um radical sir12r13r14, r2 são idênticos ou diferentes e representam, por exemplo, c1-c8-alquila, r3 são idênticos ou diferentes e representam, por exemplo, c1-c8-alquila, ou ambos os radicais r3 representam, em conjunto, c1-c4-alquenila linear que é não substituída ou porta 1 a 6 grupos metila como substituintes.

    PROCESO PARA PRODUCIR 2'-O-FUCOSIL LACTOSA.
    7.
    发明专利
    PROCESO PARA PRODUCIR 2'-O-FUCOSIL LACTOSA. 未知

    公开(公告)号：MX2018009515A

    公开(公告)日：2018-09-05

    申请号：MX2018009515

    申请日：2017-02-02

    Applicant: BASF SE

    Inventor： WOLFGANG SIEGEL ,  STEPHANIE RENZ ,  MICHAEL PUHL ,  ANDREAS WOELFERT

    IPC: C07H1/00 ,  A23C9/20 ,  A23L33/00 ,  C07H3/06 ,  C07H15/18 ,  C07H23/00

    Abstract: La presente invención se refiere a un método para preparar 2'-O-fucosil lactosa, en donde los intermediarios se obtienen mediante este método y el uso de estos intermediarios. La preparación comprende la reacción de una fucosa protegida de la Fórmula general (I) con un yoduro de tri(C1-C6-alquil)sililo para obtener una 1-iodofucosa protegida, y luego la reacción de la 1-iodofucosa protegida con un compuesto de la Fórmula general (II), en presencia de al menos una base, y la desprotección del producto de acoplamiento resultante para obtener 2'-O-fucosil lactosa. (ver Formulas). En este contexto, las variables se definen de la siguiente manera: Ra y Rb son iguales o diferentes, y son -C(=O)-C1-C6-alquilo o -C(=O)-fenilo, en donde dicho fenilo es no sustituido o tiene, opcionalmente, 1 a 5 sustituyentes, o Ra y Rb juntos son un radical (C=O) o un radical metileno sustituido C(RdRe), Rc es un radical RSi o es bencilo, en donde dicho bencilo es no sustituido o tiene, opcionalmente, 1, 2 o 3 sustituyentes, RSi es un radical de la Fórmula SiRfRgRh, en donde Rf, Rg y Rh son iguales o diferentes y son C1-C8-alquilo, por ejemplo, R1 es un radical -C(=O)-R11 o un radical SiR12R13R14, R2 son iguales o diferentes y son C1-C8-alquilo, por ejemplo; R3 son iguales o diferentes y son, por ejemplo, C1-C8-alquilo, o ambos radicales R3 juntos forman un C1-C4-alquenilo lineal, que es no sustituido o tiene 1 a 6 grupos metilo como sustituyentes.

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