CAS: 3646-73-9; (2S,3R,4S,5R,6R)-6-(Hydroxymethyl)Tetrahydro-2H-Pyran-2,3,4,5-Tetraol

该化合物是一种单沙律和C-4葡萄糖的缩记,通常在自然界中发现,它是甘蓝蛋白,甘蓝脂和多沙罗酸的组成部分,在细胞识别和信号等生物过程中发挥着关键作用.这种乙氧糖广泛用于生物化学研究,特别是在涉及碳水化合物新陈代谢,酶学实验和遗传生物学的研究中.它的高度纯度和稳定性使它适合于医药,诊断和食品科学的应用.α-D-甘油也被用作银细胞和其他酶的子体.其明确界定的结构和可靠性能确保实验和工业应用的一致性.

结构式图片

上下游产品

stachyose D-raffinose 2-chloroethyl 1-thio-β-D-galactopyranoside o-nitrophenyl D-galactopyranoside1,2,3,4,6-penta-O-benzoyl-α-D-galactopyranoside O1,O2-isopropylidene-O3,O4-phenylboranediyl-α-D-galactopyranoseO1,O2-isopropylidene-O3,O4-phenylboranediyl-α-D-galactopyranose 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 1,2,3,4,6-penta-O-trimethylsilyl-α-D-galactose

合成工艺路线路线简述

    📜双丙酮半乳糖置于硫酸体系中,用 水 作为反应溶剂,化学反应 1.0H,以21.3 G的收率获得产物alpha-D-半乳糖
    参考文献:从阿拉伯胶中分离l-阿拉伯糖和d-半乳糖的改进方法
    标题:从阿拉伯胶中分离l-阿拉伯糖和d-半乳糖的改进方法
    摘要:然后必须通过离子交换树脂 9-11 或柱色谱法进行分离.12,13 另一个描述了通过酶水解和用酵母选择性发酵阿拉伯木聚糖来制备 1 和 3 通过用特定酵母或细菌接种含有乳糖的溶液来制备. 15 这些方法产量低,效率低;此外,存在与多步骤程序相关的问题以及由于处置浪费而增加的生产成本.由于需要大量溶剂,使用这些程序中固有的离子交换或色谱法进行工业放大等限制,迫切需要设计一种新的,实用且有效的 1 和 3 的大规模制备方法,从自然且易于获取的来源开始.我们现在报告通过水解,过滤,蒸发,缩醛化,萃取,脱缩醛化和结晶组成的程序从阿拉伯树胶制备 1 和 3.这些操作很容易大规模地进行;使用的溶剂可以循环使用,并且在该过程中使用廉价的试剂.因此,我们的程序比柱方法便宜,并且可以
    DOI:10.1080/00304948.2013.798574

    海关参考信息

    专利信息


    专利号:WO-0142264-A1
    优先权日:1999-12-10
    标 题 :Method for the synthesis of sialylated oligosaccharide donors
    发明人:MEHTA SEEMA; GILBERT MICHEL; WAKARCHUK WARREN W; WHITFIELD DENNIS M
    权利人:CA NAT RESEARCH COUNCIL; MEHTA SEEMA; GILBERT MICHEL; WAKARCHUK WARREN W; WHITFIELD DENNIS M
    摘要:A method for the synthesis of aryl thioglycosides comprising a sialylated residue of β-D-galactose is disclosed. The method consists of preparing by a chemical synthesis a non-sialylated aryl thioglycoside, and enzymatically sialylating the latter with a sialic acid in the presence of a suitable sialyltransferase. The sialylated aryl thioglycoside is then chemically derivatized by standard procedures, to provide a derivative suitable for use as a donor in chemical syntheses of sialylated oligosaccharides. The derivatized sialylated aryl thioglycosides are prepared in high yields, due to reduced number of chemical and purification steps involved in the process. Derivatized aryl thioglycosides useful as building blocks for the synthesis of biologically active sialylated oligosaccharides are also disclosed.

    专利号:US-2019315790-A1
    优先权日:2016-11-11
    标题:Synthesis of d-allulose
    发明人:KOCH TIMO JOHANNES; KIPPING FLORIAN; BUTZ STEFFEN; LESCH MARCEL; HÄSSLER THOMAS
    权利人:PFEIFER & LANGEN GMBH & CO KG
    摘要:The invention relates to a process for the synthesis of a product saccharide, preferably of D-allulose from an educt saccharide, preferably from D-fructose under heterogeneous or homogeneous catalysis which includes chemical and/or enzymatic catalysis. The synthesis is performed in at least two reactors that are arranged in series and the reaction product exiting the first reactor is subjected to chromatographic separation before it enters the second reactor. Preferably, the chromatographic separation is integrated in a simulated moving bed.

    专利号:US-2004058888-A1
    优先权日:2000-01-13
    标题:Methods for synthesis of alpha-d-gal (1~>3) gal-containing oligosaccharides
    发明人:BORNAGHI LAURENT; DEKANY GYULA; DRINNAN NICHOLAS BARRY; PAPAGEORGIOU JOHN; WEST MICHAEL LEO
    摘要:This invention relates to reagents and methods for synthesis of biologically active di- and tri-saccharides comprising α-D-Gal(1→3)-D-Gal. In particular the invention provides novel reagents, intermediates and processes for the solution or solid phase synthesis of α-D-galactopyranosyl-(1→3)-D-galactose, and derivatives thereof. In one preferred embodiments the invention provides a protected monosaccharide building block of general formula (II): in which R 3 is methoxy or methyl; R 1 is H, benzoyl, pivaloyl, 4-chlorobenzoyl, acetyl, chloroacetyl, levulinoyl, 4-methylbenzoyl, benzyl, 3,4-methylenedioxybenzyl, 4-methoxybenzyl, 4-chlorobenzyl, 4-acetamidobenzyl, or 4-azidobenzyl; and R 2 is H, Fmoc, benzoyl, pivaloyl, 4-chlorobenzoyl, acetyl, chloroacetyl, levulinoyl, 4-methylbenzoyl, benzyl, 3,4-methylenedioxybenzyl, 4-methoxybenzyl, 4 -chlorobenzyl, 4-acetamidobenzyl, or 4-azidobenzyl.

    专利号:US-10751419-B2
    优先权日:2014-05-01
    标题:Method for synthesis of reactive conjugate clusters
    发明人:MIGAWA MICHAEL T; YU JINGHUA; WAN W BRAD; PATEL SAYTEN P; VASQUEZ GUILLERMO; KINBERGER GARTH A; PRAKASH THAZHA P; SETH PUNIT P; SWAYZE ERIC E
    权利人:IONIS PHARMACEUTICALS INC
    摘要:Provided herein are improved methods for the synthesis of reactive conjugate clusters and intermediates used in such methods. In particular, improvements are provided that enhance the synthesis of reactive conjugate clusters by reducing the number of synthetic steps required. The reactive conjugate clusters prepared using the improved methods don't include any transacylation impurities that are formed using existing methods. The improved methods also provide an increase in overall yield and a cost benefit over existing methods.

    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-6156885-A
    优先权日:1997-10-30
    标 题 :Process for the synthesis of alkylpolyglucosides
    发明人:MERONI MARIA LUISA; PELLIZZON TULLIO
    权利人:CONDEA AUGUSTA SPA
    摘要:The process for the synthesis of an alkylpolyglucoside having the formula (I): n n H--(G).sub.n --O--R-- (I) n n wherein n R is linear or branched, saturated or unsaturated C 8 -C 20 alkyl; n G is a radical resulting from removal of a molecule of water from a monosaccharide; and n n is an integer from 1 to 5; n the process entailing reacting an alcohol with a monosaccharide or a compound capable of generating a monosaccharide in in situ, wherein the reaction is carried out in the presence of a catalyst consisting of one or more sterically hindered polyalkylarylsulfonic acids.

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    ✅ COA系统入驻 | 共享模式

    主要参考文献


    1: Coelho AI, Berry GT, Rubio-Gozalbo ME. Galactose metabolism and health. Curr Opin Clin Nutr Metab Care. 2015 Jul;18(4):422-7. doi: 10.1097/MCO.0000000000000189. Review. doi: 10.3109/13813455.2014.962547. Epub 2014 Sep 30. doi: 10.1016/j.neuropharm.2013.09.002. Epub 2013 Sep 18. doi: 10.1021/bi500656m. Epub 2014 Jul 7.
    5: Kamthan M, Kamthan A, Ruhela D, Maiti P, Bhavesh NS, Datta A. Upregulation of galactose metabolic pathway by N-acetylglucosamine induced endogenous synthesis of galactose in Candida albicans. Fungal Genet Biol. 2013 May;54:15-24. doi: 10.1016/j.fgb.2013.02.006. Epub 2013 Feb 27. doi: 10.1371/journal.pcbi.1004017. eCollection 2014 Dec.
    7: Wang R, Wu XZ. Roles of galactose 3'-O- sulfation in signaling. Glycoconj J. 2014 Nov;31(8):549-54. doi: 10.1007/s10719-014-9558-2. Epub 2014 Oct 8. Review. Review. Japanese. doi: 10.1371/journal.pone.0070410. Print 2013.

    合成参考文献


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    参考文献:10.1021/jf9040047
    摘要:Spadiut O, Nguyen TT, Haltrich D. Thermostable variants of pyranose 2-oxidase showing altered substrate selectivity for glucose and galactose. J Agric Food Chem. 2010 Mar 24;58(6):3465–71. doi: 10.1021/jf9040047.
    参考文献:10.1186/1743-422x-7-38
    摘要:Van Poucke SG, Nicholls JM, Nauwynck HJ, Van Reeth K. Replication of avian, human and swine influenza viruses in porcine respiratory explants and association with sialic acid distribution. Virology Journal. 2010 Feb 16;7(1):38. doi: 10.1186/1743-422x-7-38.
    参考文献:10.1016/j.devcel.2009.12.018
    摘要:Kitamura E, Tanaka K, Komoto S, Kitamura Y, Antony C, Tanaka TU. Kinetochores Generate Microtubules with Distal Plus Ends: Their Roles and Limited Lifetime in Mitosis. Developmental Cell. 2010 Feb;18(2):248–59. doi: 10.1016/j.devcel.2009.12.018.
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