5-(iodomethyl)-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran | 70981-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 5-(iodomethyl)-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran
• 英文别名: 6-deoxy-1,2,3,4-di-O-isopropylidene-6-iodo-α-L-galactopyranose；(3aS,5R,5aS,8aR,8bS)-5-(iodomethyl)-2,2,7,7-tetramethyltetrahydro-3aH-bis [1,3]dioxolo[4,5-b:4′5′-d]pyran；6-iodofucose diacetonide；6-iodo-O¹,O²;O³,O⁴-diisopropylidene-α-L-6-deoxy-galactopyranose
• CAS: 70981-53-2
• 化学式: C₁₂H₁₉IO₅
• 分子量: 370.184
• InChiKey: JMIGDGVTFPSEMQ-MBXMOIHESA-N

物化性质

• 沸点：
  366.6±37.0 °C(Predicted)
• 密度：
  1.499±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-(iodomethyl)-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran 在 cyanocobalamin 、 氯化铵 、 锌 作用下， 以 甲醇 为溶剂， 以55%的产率得到5,6-Dideoxy-1,2:3,4-di-O-isopropylidene-D-arabino-5-hexenose
  参考文献：
  名称：

  锌介导的 6-Deoxy-6-iodopyranoside 片段化的维生素 B12 催化：ω-不饱和己糖衍生物（5-己烯糖）的温和且方便的制备

  摘要：

  已知的通过6-碘吡喃糖苷断裂合成5-己烯糖的锌介导方法，在维生素B12用作催化剂时，可以以简单、快速和温和的方式进行，且副反应较少。

  DOI：

  10.1055/s-2000-6305
• 作为产物：
  描述：

  alpha-D-半乳糖 在 咪唑 、 硫酸 、 碘 、 三苯基膦 、 zinc(II) chloride 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 5-(iodomethyl)-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran
  参考文献：
  名称：

  Hydrophobic d-galactose based ionic liquid for the sequestration of Pb2+ ions from aqueous solution

  摘要：

  Herein we report the synthesis of new hydrophobic ionic liquid by simple manipulations starting from D-galactose. The synthesized ionic liquid 1-methy1-3-(((3aS,5S,5aR,SaR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)14,5-b:4',5'-d]pyran-5-yl)methyl)-1H-imidazol-3-ium hexafluorophosphate(V) (IL 5) was completely characterized by sophisticated analytical techniques. IL 5 was investigated as adsorbent for the sequestration of Pb2+ ions from aqueous solution and this is proved as its potential application. Batch mode studies were done, by varying the batch parameters such as pH, IL dose, contact time, initial metal ion concentration and temperature. Various mathematical models such as kinetic models and isotherms were employed to understand the mechanism of sequestration. Thermodynamic investigations suggest that the sequestration of Pb2+ ions is spontaneous and exothermic in nature. The maximum loading capacity of IL 5 was found to be 374.9 mg g(-1). Desorption and regeneration analysis revealed the repeated use of IL 5 in industrial processes. These results suggest that IL 5 is a potential sorbent for the elimination of Pb2+ ions from aqueous solution. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molliq.2015.11.060

文献信息

• Synthesis and applications of carbohydrate based chiral ionic liquids as chiral recognition agents and organocatalysts
  作者：Nirmaljeet Kaur、Harish Kumar Chopra

  DOI：10.1016/j.molliq.2019.111994

  日期：2020.1

  Chiral ionic liquids (CILs) have shown a wide range of applications in variety of domains in chemistry. Because of this, synthesis and applications of CILs have always been areas of interest for research in the last 20 years. Present work describes, the synthesis of six carbohydrate based chiral ionic liquids (CCILs) by following simple procedures and their applications. Structures of the CCILs were

  手性离子液体（CIL）在化学领域中显示出广泛的应用范围。因此，在过去的20年中，CIL的合成和应用一直是研究的关注领域。本工作描述了通过以下简单程序及其应用合成六种基于碳水化合物的手性离子液体（CCIL）。CCIL的结构已通过各种分析技术（如NMR光谱法（1 H，13 C，11 B，31 P，19 F），EI-MS和极化法）确认。使用Mosher's酸的钠盐作为模型底物，对设计的CCIL作为手性识别剂进行了测试，直到19F NMR光谱。此外，CCIL在芳香族手性酮的对映选择性还原中用作有机催化剂，以得到相应的手性仲醇。
• METHODS AND COMPOSITIONS FOR MAKING ANTIBODIES AND ANTIBODY DERIVATIVES WITH REDUCED CORE FUCOSYLATION
  申请人：Seattle Genetics, Inc.

  公开号：US20140031536A1

  公开（公告）日：2014-01-30

  The invention provides methods and compositions for preparing antibodies and antibody derivatives with reduced core fucosylation.

  这项发明提供了一种减少核心岩藻糖基化的抗体和抗体衍生物制备的方法和组合物。
• Synthesis and biological activity of potential antimetabolites of L-fucose
  作者：Jesse A. May、Alan C. Sartorelli

  DOI：10.1021/jm00194a017

  日期：1979.8

  6-Substituted 6-deoxy-L-galactose (L-fucose) derivatives were synthesized as potential antimetabolites of L-fucose. The cytotoxic effects of these compounds were evaluated on P388 leukemia cells in culture. The L-fucose analogues which showed the most potent growth inhibition were the sulfonyl ester, bromo, and iodo derivatives; since these compounds were all capable of alkylation, it is conceivable

  合成6-取代的6-脱氧-L-半乳糖（L-岩藻糖）衍生物作为L-岩藻糖的潜在抗代谢物。评价了这些化合物对培养中的P388白血病细胞的细胞毒性作用。显示出最强的生长抑制作用的L-岩藻糖类似物是磺酰基酯，溴和碘衍生物。由于这些化合物都能够烷基化，因此可以认为它们的细胞毒性作用是这种性质的结果。与该解释一致，合成的试剂均未显示出对L- [3H]岩藻糖掺入糖蛋白的特异性抑制。
• Synthesis of GDP-Fucose on a Soluble Support: A Donor Substrate for the Fucosyltransferases
  作者：Richard Daniellou、Christine Le Narvor

  DOI：10.1002/adsc.200505170

  日期：2005.11

  The synthesis of GDP-fucose on a poly(ethylene glycol)-based soluble support is described. Our strategy relies on the attachment of the 6-deoxy-6-thio-L-galactose onto the polymer via a thioether linkage , and its conversion to GDP-fucose using established methods. We thus obtained GDP-fucose bound to the polymer that was tested as an acceptor for the recombinant fucosyltranferase FucT-III.

  描述了基于聚（乙二醇）的可溶性载体上的GDP-岩藻糖的合成。我们的策略依赖于6-脱氧-6-硫代-L-半乳糖通过硫醚键连接到聚合物上，并使用既定方法将其转化为GDP-岩藻糖。因此，我们获得了与聚合物结合的GDP-岩藻糖，被测试为重组岩藻糖基转移酶FucT-III的受体。