CAS: 79831-76-8; (1S,6S,7R,8R,8Ar)-Octahydroindolizine-1,6,7,8-Tetraol

该化合物是澳大利亚树卡斯塔诺斯珀穆姆的种子产生的一种自然产生的藻类,以其结构上与甘蔗糖相似而闻名,被归类为某些甘蓝糖,特别是甘蓝的强烈抑制剂.这一特征使其对生物化学研究和潜在的治疗应用感兴趣,特别是在病毒感染和糖尿病管理方面.该化合物展示了一种特定的立体化学,有助于其生物活动.(+)-卡斯塔诺斯珀里尼通常是一种白色的到非白晶状的固体,水和各种有机溶剂中溶液溶液.其分子配方反映了一种复杂的结构,其中包括多种羟基组,加强了其活性和与生物巨型分子的相互作用.由于其生物意义,因此已经研究过它可能在调制甘蓝合成中发挥的作用及其在药物发展中的影响.然而,像许多藻类一样,它也可能在较高浓度时表现出毒性,需要谨慎处理和在研究及治疗中考虑到.

结构式图片

物理性质

MSDS等安全信息

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

CAS号131722-89-9 (1S,6S,7R,8R,8a... | CAS号141117-12-6 Celgosivir hydr... | CAS号121104-96-9 西戈斯韦 | CAS号134100-29-1 6-ACETAMIDO-6-D...

合成工艺路线路线简述

  • 1166871-20-0 = 79831-76-8
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Ethanol; Rt
    标题:Asymmetric Synthesis Of (+)-Castanospermine Through Enol Ether Metathesis-Hydroboration/oxidation
    作者:Ceccon,Julien; Et Al
    参考文献:Organic & Biomolecular Chemistry 日期:2009 卷标:7(10) 页码:2029-2031]

    133473-23-1 = 79831-76-8
    反应条件:1.1 Reagents: Dowex 50W-X8 Solvents: Tetrahydrofuran,Water; Overnight,Reflux
    标题:Simple Total Syntheses Of (+)-Castanospermine And (+)-6-Epicastanospermine Using Indium-Mediated Allylation
    作者:Kim,Jin Hyo; Et Al
    参考文献:Synthesis 日期:2003 卷标:(16) 页码:2473-2478]

    182697-87-6 = 79831-76-8
    反应条件:1.1 Catalysts: Palladium Solvents: Formic Acid,Methanol
    标题:Allylated Monosaccharides As Precursors In Triple Reductive Amination Strategies: Synthesis Of Castanospermine And Swainsonine
    作者:Zhao,Hang; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2001 卷标:66(5) 页码:1761-1767]

    = 79831-76-8
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Methanol,Water; 24 H,Rt
    标题:Stereoselective Total Syntheses Of (+)-Castanospermine And Neu5Ac Methyl Ester
    作者:Myeong,In-Soo; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2019 卷标:84(7) 页码:4211-4220]

    1255955-59-9 = 79831-76-8
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Chloride Solvents: Ethanol; 3 H,1 Atm,Rt1.2 Solvents: Water; 30 Min,Rt
    标题:Diastereoselective Nitrenium Ion-Mediated Cyclofunctionalization: Total Synthesis Of (+)-Castanospermine
    作者:Bowen,Edward G.; Et Al
    参考文献:Organic Letters 日期:2010 卷标:12(22) 页码:5330-5333]

    531515-12-5 = 79831-76-8
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethyl Acetate; 24 H,Rt1.2 Reagents: Trifluoroacetic Acid Solvents: Water; 10 H,Rt1.3 Reagents: Dowex 1X Solvents: Water
    标题:Asymmetric Synthesis Of (+)-1-Deoxynojirimycin And (+)-Castanospermine
    作者:Somfai,Peter; Et Al
    参考文献:Tetrahedron 日期:2003 卷标:59(8) 页码:1293-1299]

    899431-83-5 = 79831-76-8
    反应条件:1.1 Reagents: Trifluoroacetic Acid Solvents: Water; 2.5 H,25 °C1.2 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol; 12 H,80 Psi
    标题:Intramolecular 5-Endo-Trig Aminomercuration Of β-Hydroxy-γ-Alkenylamines: Efficient Route To A Pyrrolidine Ring And Its Application For The Synthesis Of (+)-Castanospermine And Analogues
    作者:Karanjule,Narayan S.; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2006 卷标:71(12) 页码:4667-4670]

    857860-17-4 = 79831-76-8
    反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran; Overnight,Rt1.2 Reagents: Water; 5 Min,Rt
    标题:Novel Synthesis Of Castanospermine And 1-Epicastanospermine
    作者:Cronin,Linda; Et Al
    参考文献:Organic Letters 日期:2005 卷标:7(13) 页码:2691-2693]

    102487-68-3 = 79831-76-8
    反应条件:1.1 Reagents: (T-4)-Trihydro(Tetrahydrofuran)Boron Solvents: Tetrahydrofuran
    标题:Total Synthesis Of (+)-Castanospermine From D-Mannose
    作者:Setoi,Hiroyuki; Et Al
    参考文献:Tetrahedron Letters 日期:1985 卷标:26(38) 页码:4617-20]

    111410-12-9 = 79831-76-8
    反应条件:1.1 Reagents: Triethylamine,Methanesulfonyl Chloride Solvents: Dichloromethane1.2 Reagents: Hydrogen Catalysts: Palladium
    标题:Chelate Selectivity In Chelation-Controlled Allylations. A New Synthesis Of Castanospermine And Other Bioactive Indolizidine Alkaloids
    作者:Hamana,Hiroshi; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1987 卷标:52(24) 页码:5492-4]

    133473-17-3 = 79831-76-8 [标题:Reaction Conditions
    标题:2-Amino-2-Deoxyhexoses As Chiral Educts For Hydroxylated Indolizidines. Synthesis Of (+)-Castanospermine And (+)-6-Epicastanospermine
    作者:Gerspacher,Marc; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1991 卷标:56(11) 页码:3700-6]

    136904-86-4 = 79831-76-8 [标题:Reaction Conditions
    标题:Product Subclass 7: Aluminum Amides
    作者:Ooi,T.; Et Al
    参考文献:Science Of Synthesis 日期:2004 卷标:7 页码:225-246]

    1018472-29-1 = 79831-76-8
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Chloride Solvents: Methanol; 1 H,Rt
    标题:Synthesis Of Castanospermine
    作者:Machan,Theeraphan; Et Al
    参考文献:Tetrahedron 日期:2008 卷标:64(12) 页码:2725-2732]

    1018472-29-1 = 79831-76-8
    反应条件:1.1 Reagents: Formic Acid Catalysts: Palladium Solvents: Methanol; 4 H,Rt1.2 Solvents: Water
    标题:A Flexible Approach To Azasugars: Asymmetric Total Syntheses Of (+)-Castanospermine,(+)-7-Deoxy-6-Epi-Castanospermine,And (+)-1-Epi-Castanospermine
    作者:Liu,Gang; Et Al
    参考文献:Chemistry - A European Journal 日期:2010 卷标:16(19) 页码:5755-5768]

    129390-69-8 = 79831-76-8
    反应条件:1.1 Reagents: Hydrogen,Hydrochloric Acid Catalysts: Palladium Solvents: Methanol,Water; 48 H,Rt
    标题:A Concise Synthesis Of Castanospermine By The Use Of A Transannular Cyclization
    作者:Jensen,Thomas; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2009 卷标:74(22) 页码:8886-8889]

    182697-87-6 = 79831-76-8
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol; 4 H,1 Atm,Rt
    标题:A Concise Sequential Photochemical-Metathesis Approach For The Synthesis Of (+)-Castanospermine And Possible Uniflorine-A Stereoisomers
    作者:Zhao,Zhiming; Et Al
    参考文献:Tetrahedron 日期:2005 卷标:61(37) 页码:8888-8894]

    1166871-25-5 = 79831-76-8
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Ethanol; Rt
    标题:Asymmetric Synthesis Of (+)-Castanospermine Through Enol Ether Metathesis-Hydroboration/oxidation
    作者:Ceccon,Julien; Et Al
    参考文献:Organic & Biomolecular Chemistry 日期:2009 卷标:7(10) 页码:2029-2031]

    136904-95-5 = 79831-76-8
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Methanol
    标题:A Total Synthesis Of (+)-Castanospermine
    作者:Ina,Hiroji; Et Al
    参考文献:Tetrahedron Letters 日期:1991 卷标:32(33) 页码:4147-50]

    150661-48-6 = 79831-76-8
    反应条件:1.1 Reagents: Trifluoroacetic Acid Solvents: Acetonitrile,Water1.2 Reagents: Hydrogen Catalysts: Palladium,Carbon Solvents: Methanol1.3 Reagents: Ammonia,Amberlite Cg 50 Solvents: Water
    标题:Synthesis Of (+)-Castanospermine And 1-Epicastanospermine From D-Glucofuranurono-6,3-Lactone By Reformatskii Reaction
    作者:Grassberger,Vera; Et Al
    参考文献:Liebigs Annalen Der Chemie 日期:1993 卷标:(4) 页码:379-90]

    = 79831-76-8
    反应条件:1.1 Reagents: Trifluoroacetic Acid Solvents: Water
    标题:Process For The Preparation Of Castanospermine From 5-Tert-Butoxycarbonylamino-5-Deoxy-1,2-O-Isopropylidene-α-D-Glucuronolactone
    参考文献:European Patent Organization]

    = 79831-76-8
    反应条件:1.1 Reagents: Trifluoroacetic Acid1.2 Reagents: Hydrogen Catalysts: Platinum Solvents: Water
    标题:An Efficient,Highly Stereoselective Synthesis Of (+)-Castanospermine
    作者:Anzeveno,Peter B.; Et Al
    参考文献:Tetrahedron Letters 日期:1990 卷标:31(30) 页码:4321-4]

    = 79831-76-8
    反应条件:1.1 Reagents: Triethylamine,Methanesulfonyl Chloride Solvents: Dichloromethane1.2 Reagents: Hydrogen Catalysts: Palladium
    标题:Chelate Selectivity In Chelation-Controlled Allylations. A New Synthesis Of Castanospermine And Other Bioactive Indolizidine Alkaloids
    作者:Hamana,Hiroshi; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1987 卷标:52(24) 页码:5492-4]

    131722-84-4 = 79831-76-8 [标题:Reaction Conditions
    标题:Total,Asymmetric Synthesis Of (+)-Castanospermine,(+)-6-Deoxycastanospermine,And (+)-6-Deoxy-6-Fluorocastanospermine
    作者:Reymond,Jean Louis; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1991 卷标:56(6) 页码:2128-35
📜(1S,6S,7R,8R,8Ar)-8-(Benzyloxy)-1,6,7-Trihydroxyoctahydroindolizidine置于palladium On Activated Charcoal 氢气体系中,用 四氢呋喃,水 作为反应溶剂,化学反应 24.0H,以97%的收率获得产物栗精胺
参考文献:(+/-)castanospermine的高度立体选择性全合成
标题:(+/-)castanospermine的高度立体选择性全合成
摘要:提出了一种有效的合成方法,基于将溴加成7-氧杂双环[2.2.1]庚-5-烯-2-酮苄基缩醛,合成(+/-)castanospermine.
DOI:10.1016/s0040-4039(01)80287-2

海关参考信息

专利信息


专利号:US-7122693-B2
优先权日:1988-04-11
标题 :Acetaldehyde acetal compounds, their synthesis, and uses thereof
发明人：BELLEAU EXECUTRIX OF ESTATE PI; DIXIT DILIP M; NGUYEN-BA NGHE
权利人:SHIRE BIOCHEM INC
摘要:The acetaldehyde compounds, 2-thiobenzoylacetaldehyde diethylacetal, 2-benzoyloxyacetaldehyde bis(2-methoxyethyl)acetal, 2-hydroxyacetaldehyde bis( 2-methoxyethyl)acetal, 2-thiobenzoylacetaldehyde bis(2-methoxy-ethyl)acetal, and 2-thioacetaldehyde bis(2-methoxyethyl)acetal, are useful as intermediates in the synthesis of substituted 1,3-oxathiolanes and substituted 1,3-dioxolanes.

专利号:US-4861892-A
优先权日:1988-02-12
标题:Method for synthesis of deoxymannojirimycin
发明人：FLEET GEORGE W J
权利人:SEARLE & CO
摘要:A method is disclosed for the chemical synthesis of 1,5-dideoxy-1,5-imino-D-mannitol or 1,5-dideoxy-1,5-imino-L-mannitol from, respectively, 2,3-O-isopropylidene-L-gulono-γ-lactone or 2,3-O-isopropylidene-D-gulono-γ-lactone which comprises carrying out interconversion between the L-gulono and D-mannono forms or between the D-gulono and L-mannono forms, respectively, and connecting of C-1 to C-5 by nitrogen.

专利号:US-2010261876-A1
优先权日:2007-09-25
标 题:Novel methods of synthesis for therapeutic antiviral peptides
发明人：BRAY BRIAN L; JOHNSTON BARBARA E; SCHNEIDER STEPHEN E; TVERMOES NICOLAI A; ZHANG HUYI; FRIEDRICH PAUL E
权利人:BRAY BRIAN L; JOHNSTON BARBARA E; SCHNEIDER STEPHEN E; TVERMOES NICOLAI A; ZHANG HUYI; FRIEDRICH PAUL E
摘要:Provided herein are methods for synthesis of peptides. In particular, provided herein are methods of synthesis for therapeutic antiviral peptides.

专利号:WO-9636627-A1
优先权日:1995-05-19
标 题 :Collection of activated glycoside compounds and their biological use
发明人：ANDERSON MARK BRIAN; MUSSER JOHN H
权利人:GLYCOMED INC
摘要:The present invention relates to the field of combinatorial carbohydrate chemistry and involves the modification of organic molecules and/or the synthesis of large numbers of products comprising carbohydrate and/or glycominetic entities. More specifically, the present invention relates to activated carbon glycosides useful for the modification of organic molecules by incorporation of carbohydrate units, providing the synthesis of large numbers of products having novel chemical characteristics. The present invention further relates to methods for the generation of chemical compounds comprising carbon glycosides. Methods are disclosed to provide large arrays of molecules and to identify species that act as agonists or antagonists of various biological, chemical, and other activities.

专利号:WO-2023008461-A1
优先权日:2021-07-27
标题:Medicament for treatment and/or prevention of cancer
发明人：KUME MASAHIKO; OKANO FUMIYOSHI; SAITO TAKANORI
权利人:TORAY INDUSTRIES
摘要:The present invention relates to a medicament for the treatment and/or prevention of cancer, the medicament being characterized by comprising an antibody having an immunological reactivity with CAPRIN-1 protein or a fragment of the antibody and a drug capable of inhibiting the N-glycoside-linked sugar chain synthesis of a glycoprotein which are combined with each other in a blended or separated form.

专利号:US-2007293456-A9
优先权日:2004-12-30
标题:Method for the synthesis of 3-substituted indolizine and benzoindolizine compounds
发明人：HAYFORD ANTHONY; KALOKO JOSEPH
权利人:HAYFORD ANTHONY; KALOKO JOSEPH
摘要:A method of making a compound of Formula I: n n ncomprises reacting a compound of Formula II n n nwith a compound such as R 1 OH or R 1 SH, to produce said compound of Formula I. Compounds of Formula I are useful, among other things, as dyes, spectral sensitizers, glycosidase inhibitors, and as antibacterial, antiviral, and anti-inflammatory agents.

其他信息查阅

供应商参考报价(招募中)

品牌试剂参考报价(招募中)

实用工具

⚠️全国化工行业净网倡议书
📋制造商识别码
📖 海关编码查询
📝MSDS生成器

📌 第三方产品分析报告

✅ COA系统入驻 | 共享模式

主要参考文献


1: Hibberd AD, Clark DA, Trevillian PR, Mcelduff P. Interaction between castanospermine an immunosuppressant and cyclosporin A in rat cardiac transplantation. World J Transplant. 2016 Mar 24;6(1):206-14. doi: 10.5500/wjt.v6.i1.206.
2: Tiwari DK, Bharadwaj KC, Puranik VG, Tiwari DK. Divergent total synthesis of 1,6,8a-tri-epi-castanospermine and 1-deoxy-6,8a-di-epi-castanospermine from substituted azetidin-2-one (β-lactam), involving a cascade sequence of reactions as a key step. Org Biomol Chem. 2014 Oct 7;12(37):7389-96. doi: 10.1039/c4ob00948g. doi: 10.1016/j.trim.2012.05.002. Epub 2012 May 27. doi: 10.1002/chem.200903490. doi: 10.1021/jo300309z. Epub 2012 May 25. doi: 10.1021/ol501730p. Epub 2014 Jul 8. doi: 10.1021/jo5025283. Epub 2014 Nov 20. doi: 10.3892/or.2016.4656. Epub 2016 Mar 7. doi: 10.1371/journal.pone.0076411. eCollection 2013.
10: Hong YP, Chen C, Guo WY, Zhao L, Mei FC, Xiang MW, Wang WX. Effects of Castanospermine on Inflammatory Response in a Rat Model of Experimental Severe Acute Pancreatitis. Arch Med Res. 2016 Aug;47(6):436-445. doi: 10.1016/j.arcmed.2016.11.007.

合成参考文献


参考文献:10.1007/s00011-007-7037-y
摘要:Xu XL, Xie QM, Shen YH, Jiang JJ, Chen YY, Yao HY, Zhou JY. Mannose prevents lipopolysaccharide-induced acute lung injury in rats. Inflamm Res. 2008 Mar;57(3):104–10. doi: 10.1007/s00011-007-7037-y.
参考文献:10.1016/j.ejphar.2015.10.017
摘要:Hiramatsu R, Fukuhara S, Mitsuda S, Yokomichi T, Kataoka T. Betulinic acid and oleanolic acid, natural pentacyclic triterpenoids, interfere with N-linked glycan modifications to intercellular adhesion molecule-1, but not its intracellular transport to the cell surface. Eur J Pharmacol. 2015 Nov 15;767():126–34. doi: 10.1016/j.ejphar.2015.10.017.
参考文献:10.1042/bj2850693
摘要:Carroll R, Ben-Zeev O, Doolittle MH, Severson DL. Activation of lipoprotein lipase in cardiac myocytes by glycosylation requires trimming of glucose residues in the endoplasmic reticulum. Biochem J. 1992 Aug 01;285 ( Pt 3)():693–6.
参考文献:10.1007/bf03348723
摘要:Lash RW, Desai RK, Zimmerman CA, Flack MR, Yoshida T, Wondisford FE, Weintraub BD. Mutations of the human thyrotropin-ß subunit glycosylate site reduce thyrotropin synthesis independent of changes in glycosylate status. Journal of Endocrinological Investigation. 1992 Apr;15(4):255–63. doi: 10.1007/bf03348723.
参考文献:10.1016/s0021-9258(17)36339-1
摘要:Repp R, Tamura T, Boschek CB, Wege H, Schwarz RT, Niemann H. The effects of processing inhibitors of N-linked oligosaccharides on the intracellular migration of glycoprotein E2 of mouse hepatitis virus and the maturation of coronavirus particles. Journal of Biological Chemistry. 1985 Dec;260(29):15873–9. doi: 10.1016/s0021-9258(17)36339-1.
📝 需求与反馈
尽可能描述清楚需求与问题信息
×

通知