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.

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.

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.