5,6-anhydro-1,2-O-isopropylidene-3-O-methyl-L-idopyranose | 868078-61-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6-anhydro-1,2-O-isopropylidene-3-O-methyl-L-idopyranose
• 英文别名: 5,6-anhydro-1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose；5,6-Anhydro-1,2-O-isopropyliden-3-O-methyl-α-D-glucofuranose；(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-5-(oxiran-2-yl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 868078-61-9
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: DSECIMYUBVDHMX-HFYYSOHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6-anhydro-1,2-O-isopropylidene-3-O-methyl-L-idopyranose 在 吡啶 、 4-二甲氨基吡啶 、 硫酸 、 水 作用下， 反应 21.0h， 生成 1,2,4,6-tetra-O-acetyl-3-O-methyl-α-L-idopyranose
  参考文献：
  名称：

  Identification of a hexasaccharide sequence able to inhibit thrombin and suitable for ‘polymerisation’

  摘要：

  Three hexasaccharides, having from low to very high affinity for antithrombin, were synthesised from disaccharide building block precursors. One of them, methyl(sodium 2,3-di-O-methyl-4-O-sodium sulfonato-alpha-L-idopyranosyluronate)-(1 --> 4)-[(2,3,6-tri-O-sodium sulfonato-alpha-D-glucopyranosyl)-(1 --> 4)-(sodium 2,3-di-O-methyl-alpha-L-idopyranosyluronate)-(1 --> 4)](2)-2,3,6-tri-O-sodium sulfonato-alpha-D-glucopyranoside, obtainable from a single disaccharide building block precursor, constitutes a good starting point for obtaining simple oligosaccharidic heparin mimetics able to inhibit the two coagulation factors thrombin and Factor Xa. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00067-1
• 作为产物：
  描述：

  6-bromo-6-deoxy-1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose 在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 72.0h， 以18%的产率得到6-bromo-6-deoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-hexofuranos-5-ulose
  参考文献：
  名称：

  Synthesis and antiviral activity of azoles obtained from carbohydrates

  摘要：

  Herein we describe the synthesis of 1,2,4-triazolyl-3-thione; 1,3,4-oxadiazole, and imidazo[2,1-b]thiazole derivatives from carbohydrates. The antiviral activity of these compounds was tested against Dengue and Junin virus (the etiological agent of Argentine hemorrhagic fever). The 3-(p-bromobenzoyl)-5-(1,2-O-isopropylidene-3-O-methyl-alpha-D-xylofuranos-5-ulos-5-yl)imidazo[2,1-b]thiazole was able to inhibit the replication of both viruses in Vero cells at concentration significantly lower than the CC50. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.06.028

文献信息

• [2+2]-Cycloaddition of Chlorosulfonyl Isocyanate to (Z)-Propenyl Ethers Bound to Polystyrene Resins by Alkylsulfonyl Linkers
  作者：Robert Łysek、Barbara Grzeszczyk、Bartłomiej Furman、Marek Chmielewski

  DOI：10.1002/ejoc.200400226

  日期：2004.10

  and 5-O-(Z)-propenyl ethers derived from 1,2-O-isopropylidene-α-D-xylo- and glucofuranoses, respectively, were attached to the Merrifield, MPPC and NCPSC resins using alkylsulfonyl linkers. The [2+2]-cycloaddition of chlorosulfonyl isocyanate to the polymer-bound vinyl ethers followed by the intramolecular alkylation of the β-lactam nitrogen led to the formation of mixtures of the corresponding diastereomeric

  分别衍生自 1,2-O-异亚丙基-α-D-木糖和呋喃葡萄糖的 3-O- 和 5-O-(Z)-丙烯基醚使用烷基磺酰基接头连接到 Merrifield、MPPC 和 NCPSC 树脂上. 氯磺酰基异氰酸酯与聚合物结合的乙烯基醚的 [2+2]-环加成反应，然后是 β-内酰胺氮的分子内烷基化，导致形成具有低立体选择性的相应非对映异构体 oxacephams 或 clavams 的混合物。在 Merrifield 和 MPP 树脂的情况下，β-内酰胺伴随着相应的氧杂环丁烷或环氧乙烷。使用可溶性聚合物进行的反应与在溶液中进行的反应类似。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Synthesis and Anticoagulant Activity of Bioisosteric Sulfonic-Acid Analogues of the Antithrombin-Binding Pentasaccharide Domain of Heparin
  作者：Mihály Herczeg、László Lázár、Zsuzsanna Bereczky、Katalin E. Kövér、István Timári、János Kappelmayer、András Lipták、Sándor Antus、Anikó Borbás

  DOI：10.1002/chem.201201041

  日期：2012.8.20

  were related to the antithrombin‐binding domain of heparin were prepared, in which two or three primary sulfate esters were replaced by sodium‐sulfonatomethyl moieties. The sulfonic‐acid groups were formed on a monosaccharide level and the obtained carbohydrate sulfonic‐acid esters were found to be excellent donors and acceptors in the glycosylation reactions. Throughout the synthesis, the hydroxy groups

  制备了两种与肝素抗凝血酶结合域有关的五糖磺酸，其中两个或三个伯硫酸酯被钠磺酰甲基部分取代。磺酸基团是在单糖水平上形成的，发现所获得的碳水化合物磺酸酯是糖基化反应中的优良供体和受体。在整个合成过程中，将要甲基化的羟基以乙酸酯的形式掩蔽，将要硫酸化的羟基用苄基掩蔽。通过使用三糖二磺酸作为受体和葡糖醛酸二糖作为供体，以[2 + 3]嵌段合成的方式制备二磺酸类似物。为了合成五糖三磺酸，一种更有效的方法，详细说明了该过程，包括用未氧化的葡萄糖醛酸前体延长三糖受体，然后在四糖水平进行糖苷后氧化，然后进行[1 + 4]偶联反应。对这些新的磺酸衍生物的抗凝活性的体外评估表明，二磺酸盐类似物具有出色的抑制血凝蛋白酶因子Xa的作用。然而，引入第三个磺酸部分导致抗Xa活性显着下降。二磺酸和三磺酸对应物在生物活性上的差异可以用它们的不同构象来解释。对这些新的磺酸衍生物的抗凝活性的体外评估表明，二磺酸盐类似物具有出
• Surface and Self‐Aggregation Properties of Bis‐Benzimidazolones Derivatives of <scp>d</scp> ‐Glucose
  作者：Brahim Lakhrissi、Loubna Lakhrissi、Mohamed Massoui、El Mokhtar Essassi、Francesc Comelles、Jordi Esquena、Conxita Solans、Carlos Rodríguez‐Abreu

  DOI：10.1007/s11743-010-1183-x

  日期：2010.7

  area per molecule at the interface, and critical micelle concentration (CMC) were found to be significantly dependent on the hydrophobic alkyl chain length. The synthesized compounds form micelles at remarkably low concentrations, and CMCs derived from surface tension measurements show a minimum as a function of the alkyl chain length; this unusual trend can be attributed to the formation of submicellar

  一系列新的两亲同系物d的双苯并咪唑酮衍生物的表面和自聚集性质研究了葡萄糖。发现诸如最大表面过量浓度，界面上每个分子的最小面积以及临界胶束浓度（CMC）等参数显着取决于疏水性烷基链长度。合成的化合物以非常低的浓度形成胶束，并且源自表面张力测量的CMC显示出的最小值是烷基链长的函数；如荧光探针光谱数据所证明的，这种不寻常的趋势可归因于在具有长烷基链的化合物中形成了亚胶束聚集体。在高表面活性剂浓度下，形成具有六方结构的溶致液晶相。
• [EN] ANTICOAGULANT PENTASACCHARIDE COMPOUND, COMPOSITION, AND PREPARATION METHOD AND MEDICAL USE THEREOF<br/>[FR] COMPOSÉ DE PENTASACCHARIDE ANTICOAGULANT, COMPOSITION, PROCÉDÉ DE PRÉPARATION CORRESPONDANT ET UTILISATION MÉDICALE ASSOCIÉE<br/>[ZH] 抗凝血的五糖类化合物、组合物及其制备方法和医药用途
  申请人：NANJING CHIA TAI TIANQING PHARMACEUTICAL CO LTD

  公开号：WO2020114418A1

  公开（公告）日：2020-06-11

  本发明涉及其阴离子形式如式（A）所示的抗凝血化合物、其制备方法以及其在制备预防和/或治疗与血液凝固障碍相关的疾病的药物中的用途。
• Synthesis and antiviral activity of azoles obtained from carbohydrates
  作者：José Sebastián Barradas、María Inés Errea、Norma B. D’Accorso、Claudia S. Sepúlveda、Laura B. Talarico、Elsa B. Damonte

  DOI：10.1016/j.carres.2008.06.028

  日期：2008.9

  Herein we describe the synthesis of 1,2,4-triazolyl-3-thione; 1,3,4-oxadiazole, and imidazo[2,1-b]thiazole derivatives from carbohydrates. The antiviral activity of these compounds was tested against Dengue and Junin virus (the etiological agent of Argentine hemorrhagic fever). The 3-(p-bromobenzoyl)-5-(1,2-O-isopropylidene-3-O-methyl-alpha-D-xylofuranos-5-ulos-5-yl)imidazo[2,1-b]thiazole was able to inhibit the replication of both viruses in Vero cells at concentration significantly lower than the CC50. (C) 2008 Elsevier Ltd. All rights reserved.