(4aR,6S,7R,8R,8aS)-6-(ethylthio)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol | 1202168-00-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,6S,7R,8R,8aS)-6-(ethylthio)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 1202168-00-0
• 化学式: C₁₁H₂₀O₅S
• 分子量: 264.343
• InChiKey: YHBIAKLTURNUQJ-IGORNWKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.34
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (4aR,6S,7R,8R,8aS)-6-(ethylthio)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 Hoveyda-Grubbs catalyst second generation 、 2-氯-1-甲基吡啶碘化物 、 1-羟基苯并三唑 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， -50.0~20.0 ℃ 、101.33 kPa 条件下， 反应 38.5h， 生成
  参考文献：
  名称：

  Ring Expansion Leads to a More Potent Analogue of Ipomoeassin F

  摘要：

  Two new ring-size-varying analogues (2 and 3) of ipomoeassin F were synthesized and evaluated. Improved cytotoxicity (IC₅₀: from 1.8 nM) and in vitro protein translocation inhibition (IC₅₀: 35 nM) derived from ring expansion imply that the binding pocket of Sec61α (isoform 1) can accommodate further structural modifications, likely in the fatty acid portion. Streamlined preparation of the key diol intermediate 5 enabled gram-scale production, allowing us to establish that ipomoeassin F is biologically active in vivo (MTD: ∼3 mg/kg).

  DOI：

  10.1021/acs.joc.0c01659
• 作为产物：
  描述：

  D-葡萄糖 在 高氯酸 、 乙酸酐 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.83h， 生成 (4aR,6S,7R,8R,8aS)-6-(ethylthio)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
  参考文献：
  名称：

  Ring Expansion Leads to a More Potent Analogue of Ipomoeassin F

  摘要：

  Two new ring-size-varying analogues (2 and 3) of ipomoeassin F were synthesized and evaluated. Improved cytotoxicity (IC₅₀: from 1.8 nM) and in vitro protein translocation inhibition (IC₅₀: 35 nM) derived from ring expansion imply that the binding pocket of Sec61α (isoform 1) can accommodate further structural modifications, likely in the fatty acid portion. Streamlined preparation of the key diol intermediate 5 enabled gram-scale production, allowing us to establish that ipomoeassin F is biologically active in vivo (MTD: ∼3 mg/kg).

  DOI：

  10.1021/acs.joc.0c01659

文献信息

• Synthesis of a tetrasaccharide related to the repeating unit of the O-antigen from Escherichia coli K-12
  作者：Bimalendu Roy、Robert A. Field、Balaram Mukhopadhyay

  DOI：10.1016/j.carres.2009.09.026

  日期：2009.11

  Synthesis of a tetrasaccharide related to the repeating unit of the O-antigen from Escherichia coli K-12 is reported in the form of its octyl glycoside. Syntheses of the 1,2-cis glycosidic linkages have been accomplished by using NIS in conjunction with H(2)SO(4)-silica, and it was found to be stereoselective and productive. The synthesized tetrasaccharide will be utilized as the substrate for gal

  以其辛基糖苷的形式报道了从大肠杆菌K-12合成与O-抗原的重复单元有关的四糖。1,2-顺式糖苷键的合成已通过使用NIS结合H（2）SO（4）-二氧化硅来完成，并且被发现具有立体选择性和生产性。合成的四糖将用作半乳糖呋喃糖基转移酶WbbI的底物。
• Efficient Preparation of O-Isopropylidene Derivatives of Carbohydrates Catalyzed by Sulfonated Graphene (GR-SO3H) as a Sustainable Acid Catalyst
  作者：Rajib Panchadhayee、Padmashri Rabha

  DOI：10.1055/a-2218-7604

  日期：2024.4

  (GR-SO3H) has emerged as a mild, efficient and sustainable catalyst for the preparation of O-isopropylidene derivatives of unprotected and anomeric-protected carbohydrates with acetone and 2,2-dimethoxypropane at room temperature. This methodology not only provides excellent yields but also reduces reaction times, and it demonstrates exceptional recyclability, allowing the catalyst to be reused multiple times

  磺化石墨烯（GR-SO3H）已成为一种温和、高效且可持续的催化剂，用于制备室温下，未保护和异头保护的碳水化合物与丙酮和 2,2-二甲氧基丙烷的 O-异丙叉衍生物。该方法不仅提供了优异的产率，还缩短了反应时间，并且表现出出色的可回收性，允许催化剂多次重复使用。