CAS: 3396-99-4; (2R,3R,4S,5R,6S)-2-(Hydroxymethyl)-6-Methoxytetrahydro-2H-Pyran-3,4,5-Triol

该化合物是一种具有阳极环结构的化学立体定义的甲基氧酸衍生物,该化合物的特点是特定空间方向的多种氢氧基化合物(2R,3R,3R,4S,5R,5R配置)和6位置的甲氧基化合物组,赋予独特的再活性模式.精确安排的功能组使其作为合成化学的手艺建筑块具有价值,特别是在碳水化合物合成和玻璃聚合的制备中.其立体纯度确保了在聚合和防护/防护战略中可预见的反应结果.该化合物的结构僵硬性和氢结合能力促进了分子识别研究的应用.甲氧基化合物在保持选择性修改的充分再活性的同时增强了稳定性,在复杂的分子组装方面提供了优势,而与完全氢氧类类比.

结构式图片

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CAS号3601-36-3 甲基2,3,6-三-O-苯甲酰... | CAS号26927-44-6 METHYL-2,6-DI-O... | CAS号42927-28-6 methyl 6-O-benz... | CAS号40269-01-0 3,4-O-异亚丙基-α-D-...

合成工艺路线路线简述

    Methyl 4,6-O-Benzylidene-α-D-Galactopyranoside置于tetrafluoroboric Acid体系中,用 乙腈 作为反应溶剂,化学反应 0.2H,以87.2%的收率获得产物α-D-乳酸吡喃糖苷甲酯
    参考文献:Tetrafluoroboric Acid,An Efficient Catalyst In Carbohydrate Protection And Deprotection Reactions
    标题:Tetrafluoroboric Acid,An Efficient Catalyst In Carbohydrate Protection And Deprotection Reactions
    摘要:
    DOI:10.1016/0008-6215(85)85171-5

    海关参考信息

    专利信息


    专利号:US-5532147-A
    优先权日:1991-08-06
    标题:Enzymatic method for synthesis of carbohydrates
    发明人:NILSSON KURT
    摘要:A synthetic method in which is included at least one process, which is characterized by that a glycosidase (EC 3.2) is used to catalyse a reaction between a partially protected galactose derivative, or a partially protected glucose derivative, and a glycosyl doner, which is an oligosaccharide or a monosaccharide glycoside, is described. The process is suitable for synthesis of carbohydrate derivatives or for synthesis of partially protected carbohydrate intermediates which are suitable for further synthesis e.g. of blood group determinants A and B, or other carbohydrates.

    专利号:US-5856143-A
    优先权日:1993-05-14
    标 题 :N-containing saccharides and method for the synthesis of N-containing saccharides from amino-deoxy-disaccharides and amino-deoxy-oligosaccharides
    发明人:NILSSON KURT G I
    权利人:BIOFLEXIN AB
    摘要:Synthesis of an amino-disaccharide, amino-oligosaccharide or a derivative thereof, characterized in that a monosaccharide, a disaccharide, an oligosaccharide, a glycoside or a derivative thereof, in the presence of a glycosidase as catalyst, is reacted with an amino-deoxy-saccharide or a derivative thereof, and that the amino-saccharide is isolated from the product mixture directly or after chemical/enzymatic modification.

    专利号:US-4794176-A
    优先权日:1981-06-26
    标 题 :Synthesis of tumor antigenic determinant
    发明人:LEMIEUX RAYMOND U; RATCLIFFE ROBERT M; BAKER DONALD A
    权利人:CHEMBIOMED
    摘要:Processes are provided for the synthesis of the human T-antigenic determinant 2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranoside containing an α-O-glycosidically linked bridging arm O--(CH 2 ) n COR. The determinant is coupled to carrier molecules to form artifical T-antigens, and to insoluble supports to form T-immunoadsorbents. The artificial T-antigen is shown to elicit a delayed type hypersensitivity reaction as a diagnostic for the presence of cancer in humans.

    专利号:US-4767845-A
    优先权日:1980-07-10
    标题 :Synthesis of tumor antigenic determinant
    发明人:LEMIEUX RAYMOND U; RATCLIFFE ROBERT M; BAKER DONALD A
    权利人:CHEMBIOMED LTD
    摘要:Processes are provided for the synthesis of the human T-antigenic determinant 2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranoside containing an α-O-glycosidically linked bridging arm O--(CH 2 ) n COR. The determinant is coupled to carrier molecules to form artificial T-antigens, and to insoluble supports to form T-immunoadsorbents. The artifical T-antigen is shown to elicit a delayed type hypersensitivity reaction as a diagnostic for the presence of cancer in humans.

    专利号:US-6183994-B1
    优先权日:1993-05-14
    标题:N-containing saccharides and method for the synthesis of N-containing saccharides from amino-deoxy-disaccharides and amino-deoxy-oligosaccharides
    发明人:NILSSON KURT G I
    权利人:BIOFLEXIN AB
    摘要:Synthesis of an amino-disaccharide, amino-oligosaccharide or a derivative thereof, characterized in that a monosaccharide, a disaccharide, an oligosaccharide, a glycoside or a derivative thereof, in the presence of a glycosidase as catalyst, is reacted with an amino-deoxy-saccharide or a glycoside or derivative thereof, and that the amino-saccharide is optionally isolated from the product mixture directly or after chemical/enzymatic modification.

    专利号:US-7338932-B2
    优先权日:2000-05-11
    标题 :Methods of modulating functions of polypeptide GalNAc-transferases and of screening test substances to find agents herefor, pharmaceutical compositions comprising such agents and the use of such agents for preparing medicaments
    发明人:CLAUSEN HENRIK; BENNETT ERIC PAUL; HASSAN HELLE; REIS CELSO ALBUQUERQUE
    权利人:GLYCOZYM APS
    摘要:Attachment of O-glycans to proteins is controlled by a large family of homologous polypeptide GalNAc-transferases. Polypeptide GalNAc-transferases contain a C-terminal sequence with similarity to lectins. This invention discloses that the putative lectin domains of GalNAc-transferase isoforms, GalNAc-T4, -T7, -T2, and -T3, are functional and recognize carbohydrates, glycopeptides, and peptides and discloses the lectin domains of GalNAc-T1-T16. These lectin domains have different binding specificities and modulate the functions of GalNAc-transferase isoforms differently. Novel methods for identification of inhibitors or modulators of binding activities mediated by lectin domains of polypeptide GalNAc-transferases are disclosed. Direct binding activity of GalNAc-transferase lectins has been demonstrated for the first time and methods to measure lectin mediated binding of isolated lectins or enzymes with lectin domains are disclosed. The present invention specifically discloses a novel selective inhibitor of polypeptide GalNAc-transferase lectin domains, which provides a major advancement in that this inhibitor and related inhibitors sharing common characteristics of activity bind lectin domains without serving as acceptor substrate for glycosyltransferases involved in synthesis of O-glycans. This inhibitor is represented by the β-anomeric configuration of GalNAc-benzyl, GalNAcβ-benzyl. Methods for inhibiting intracellular transport, cell surface expression, and secretion of mucins and O-glycosylated glycoproteins without affecting O-glycosylation processing are disclosed using the novel selective inhibitor identified.
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    合成参考文献


    摘要:Vashchenko, B. V.; Grygorenko, O. O., Science of Synthesis Knowledge Updates, (2021) 3, 338.
    摘要:Vashchenko, B. V.; Grygorenko, O. O., Science of Synthesis Knowledge Updates, (2021) 3, 346.
    摘要:Vashchenko, B. V.; Grygorenko, O. O., Science of Synthesis Knowledge Updates, (2021) 3, 350.
    摘要:Vashchenko, B. V.; Grygorenko, O. O., Science of Synthesis Knowledge Updates, (2021) 3, 319.
    摘要:Ewing, T. A.; Fraaije, M. W.; van Berkel, W. J. H., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 3, 177.
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