CAS: 1824-94-8; (2R,3R,4S,5R,6R)-2-(Hydroxymethyl)-6-Methoxytetrahydro-2H-Pyran-3,4,5-Triol

该化合物是一种晶体,具体地说是一种甘蔗甘蓝糖的甲基醚,其特征是分子结构,包括一个带有甲氧基碳的星际除虫菊(-OCH3)环,附于乙型结构中的厌食碳;该化合物一般是白色晶状固体,由于存在可形成水分子氢联结的氢氧化物,在水中可溶解.甲基乙型D藻类-藻类-藻类拉诺丁,经常用于生物化学研究,特别是涉及碳水化合物相互作用,酶试验的研究,以及作为各种甘烃基转移酶的子体.其甜度和低毒性使其适合用于食品用途.此外,它可作为研究寡烯酸和聚沙酸的特性的示范化合物.该化合物在正常条件下保持稳定,但可能在强酸或碱基中进行水解.

结构式图片

相似化合物

3396-99-4 29411-57-2 3149-68-6

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

甲基 β-D-吡喃葡萄糖苷 Methyl Beta-D-Glucopyranoside 709-50-2
Methyl Mannoside 22277-65-2
Lactose 63-42-3
甲基 4-O-Beta-D-半乳糖基-Beta-D-吡喃葡萄糖苷 Methyl β-D-Lactopyranoside 7216-69-5
Methyl α-L-Fucopyranosyl-(1->2)-β-D-Galactopyranoside 24656-23-3
β-半乳糖苷酶 β-D-Galactopyranoside 7296-64-2
D-吡喃葡萄糖 D-Galactose 10257-28-0
2(S)-1-O-Docosanoyl-2-O-Docosanoyl-3-O-β-D-Galactopyranosylglycerol 161777-52-2 Methyl 2,3,4,6-Tetra-O-Acetyl-β-D-Galactopyranoside 5019-23-8 Methyl 3-O-Benzyl-β-D-Galactopyranoside 40010-11-5

合成工艺路线路线简述

    β-半乳糖苷酶置于盐酸体系中,用 甲醇 用作溶剂,以98.35%的收率获得甲基-β-D-吡喃半乳糖苷
    参考文献: Improved Process For Preparation Of 2,3,4,6-Tetra-O-Benzyl-D-Galactose[fr] Procédé Amélioré De Préparation De 2,3,4,6-Tétra-O-Benzyl-D-Galactose
    标题: Improved Process For Preparation Of 2,3,4,6-Tetra-O-Benzyl-D-Galactose[fr] Procédé Amélioré De Préparation De 2,3,4,6-Tétra-O-Benzyl-D-Galactose
    摘要:本文提供了一种改进的过程,用于制备苯甲基化的d-半乳糖衍生物,特别是2,3,4,6-四-O-苯甲基-D-半乳糖,该过程提高了产量和纯度,成本效益更好,减少了杂质.

    海关参考信息

    专利信息


    专利号:US-5374541-A
    优先权日:1993-05-04
    标 题 :Combined use of β-galactosidase and sialyltransferase coupled with in situ regeneration of CMP-sialic acid for one pot synthesis of oligosaccharides
    发明人:WONG CHI-HUEY; GAETA FEDERICO C A
    权利人:SCRIPPS RESEARCH INST; CYTEL CORP
    摘要:A single reaction vessel process for the synthesis of a sialylated galactoside is disclosed. The synthesis utilizes a β-galactosidase to catalyze the reaction of a galactose-containing substrate and an acceptor to form a new galactosyl glycoside that is then sialylated using a cyclic multienzyme synthesis system to form CMP-sialic acid that sialylates the formed galactosyl glycoside in the presence of an α-sialyltransferase. The value of K m /V max for the formed galactosyl glycoside as a substrate for the α-sialyltransferase is less than one-third the K m /V max value for the galactose-containing substrate for that α-sialyltransferase.

    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-7906460-B2
    优先权日:2000-12-13
    标 题:Active-site engineering of nucleotidylyltransferases and general enzymatic methods for the synthesis of natural and “unnaturalâ€? UDP- and TDP-nucleotide sugars
    发明人:THORSON JON; NIKILOV DIMITAR B
    权利人:SLOAN KETTERING INST CANCER
    摘要:The present invention provides mutant nucleotidylyl-transferases, such as E p , having altered substrate specificity; methods for their production; and methods of producing nucleotide sugars, which utilize these nucleotidylyl-transferases. The present invention also provides methods of synthesizing desired nucleotide sugars using natural and/or modified E p or other nucleotidyltransferases; and nucleotide sugars synthesized by the present methods. The present invention further provides new glycosyl phosphates, and methods for making them.

    专利号:US-4866041-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 syntheses 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:EP-0725144-A1
    优先权日:1995-02-06
    标题 :Process for the preparation of glycosides using glycosidases from ciliates
    发明人:KIY THOMAS DR; HOERSCH BRIGITTE DR; MARQUARDT RUEDIGER DR
    权利人:HOECHST AG
    摘要:The invention relates to a process for the production of glycosides by enzymatic glycosylation by means of α- and β-glycosidases from holotrich ciliates and in particular from Hymenostomatida.n n n Glycosidases from holotrich ciliates are very well suited for the enzymatic synthesis of alkyl glycosides, glycopeptides, di- or oligosaccharides. Preferred glycosyldoren are nitrophenylglycosides, glycosyl fluorides or disaccharides, preferred acceptors are short-chain alcohols, polyhydroxy compounds, in particular monosaccharides, or protected hydroxyamino acids or corresponding peptides.
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    主要参考文献

    [参考文献]: Alexander I Zinin, Et Al. 1-O-Acetyl-Beta-D-Galactopyranose: A Novel Substrate For The Transglycosylation Reaction Catalyzed By The Beta-Galactosidase From Penicillium Sp. Carbohydr Res. 2002 Apr 2;337(7):635-42.
    [参考文献]: Andrew J Nok, Et Al. A 45-Kda Midgut Glycoprotein From Anopheles Albimanus Mosquito Mediates The Killing Of Trypanosomes. Cell Biochem Funct. 2002 Sep;20(3):257-62.
    [参考文献]: H Takesada, Et Al. The Interaction Of Elderberry (Sambucus Sieboldiana) Bark Lectin And Sialyloligosaccharides As Detected By 1H-Nmr. J Biochem. 1992 Jul;112(1):143-6.
    [参考文献]: J A Van Kuik, Et Al. Primary Structure Determination Of Seven Novel N-Linked Carbohydrate Chains Derived From Hemocyanin Of Lymnaea Stagnalis. 3-O-Methyl-D-Galactose And N-Acetyl-D-Galactosamine As Constituents Of Xylose-Containing N-Linked Oligosaccharides In An Animal Glycoprotein. Eur J Biochem. 1987 Dec 1;169(2):399-411.
    [参考文献]: Joel S Griffitts, Et Al. Glycolipids As Receptors For Bacillus Thuringiensis Crystal Toxin. Science. 2005 Feb 11;307(5711):922-5.

    合成参考文献


    摘要:Vashchenko, B. V.; Grygorenko, O. O., Science of Synthesis Knowledge Updates, (2021) 3, 338.
    摘要:Hou, W.; Yang, G.; Xu, H., Science of Synthesis: DNA-Encoded Libraries, (2024) nan, 187.
    参考文献:10.1107/s0907444999006587
    摘要:Ravishankar R, Suguna K, Surolia A, Vijayan M. Structures of the complexes of peanut lectin with methyl-beta-galactose and N-acetyllactosamine and a comparative study of carbohydrate binding in Gal/GalNAc-specific legume lectins. Acta Crystallogr D Biol Crystallogr. 1999 Aug;55(Pt 8):1375–82. doi: 10.1107/s0907444999006587.
    参考文献:10.1002/cbf.969
    摘要:Nok AJ, Njoku GC, Balogun E. A 45‐kDa midgut glycoprotein from Anopheles albimanus mosquito mediates the killing of trypanosomes. Cell Biochemistry & Function. 2002 Feb;20(3):257–62. doi: 10.1002/cbf.969.
    参考文献:10.1016/j.febslet.2008.05.035
    摘要:Jiménez M, André S, Barillari C, Romero A, Rognan D, Gabius HJ, Solís D. Domain versatility in plant AB-toxins: evidence for a local, pH-dependent rearrangement in the 2gamma lectin site of the mistletoe lectin by applying ligand derivatives and modelling. FEBS Lett. 2008 Jun 25;582(15):2309–12. doi: 10.1016/j.febslet.2008.05.035.
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