5-Deoxy-3,4-O-isopropyliden-D-arabinitol | 159247-47-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Deoxy-3,4-O-isopropyliden-D-arabinitol
• 英文别名: (1R)-1-[(4S,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol
• CAS: 159247-47-9
• 化学式: C₈H₁₆O₄
• 分子量: 176.213
• InChiKey: QIGIJTXKTYJENP-FSDSQADBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Deoxy-3,4-O-isopropyliden-D-arabinitol 在 lead(IV) acetate 作用下， 以 乙酸乙酯 为溶剂， 反应 0.25h， 以89%的产率得到4(R),5(R)-2,2,5-trimethyl-1,3-dioxolane-4-carboxaldehyde
  参考文献：
  名称：

  Eine einfache Synthese aller vier stereoisomeren 2,2,5-Trimethyl-1,3-dioxolan-4-carbaldehyde

  摘要：

  A simple and efficient procedure for the syntheses of all four stereoisomers of the 2,2,5-trimethyl-1,3-dioxolane-4-carbaldehydes 1a-1d has been developed. Starting with readily available aldopentose diethyl dithioacetals 2, 6, 10 and 14, the title compounds were obtained by a selective protecting group strategy and subsequent Raney-nickel reduction, followed by lead tetraacetate cleavage. This procedure allows an application on a multigram scale.

  DOI：

  10.1007/bf01277638
• 作为产物：
  描述：

  (2R,3S,4S)-5,5-bis(ethylthio)pentane-1,2,3,4-tetraol 在 镍 phosphorus pentoxide 、 溶剂黄146 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 4.25h， 生成 5-Deoxy-3,4-O-isopropyliden-D-arabinitol
  参考文献：
  名称：

  Eine einfache Synthese aller vier stereoisomeren 2,2,5-Trimethyl-1,3-dioxolan-4-carbaldehyde

  摘要：

  A simple and efficient procedure for the syntheses of all four stereoisomers of the 2,2,5-trimethyl-1,3-dioxolane-4-carbaldehydes 1a-1d has been developed. Starting with readily available aldopentose diethyl dithioacetals 2, 6, 10 and 14, the title compounds were obtained by a selective protecting group strategy and subsequent Raney-nickel reduction, followed by lead tetraacetate cleavage. This procedure allows an application on a multigram scale.

  DOI：

  10.1007/bf01277638

文献信息

• Synthesis of N-substituted 1,5-dideoxy-1,5-imino-L-fucitol derivatives
  申请人：G.D. SEARLE & COMPANY

  公开号：EP0363344A1

  公开（公告）日：1990-04-11

  Novel intermediates and method for the chemical synthesis of N-substituted 1,5-dideoxy-­1,5-imino-L-fucitol derivatives are provided. A preferred intermediate is 1,5-dideoxy-1,5-imino-3, 4-O-isopropylidene-L-fucitol which is used to prepare the HIV inhibitor 1,5-dideoxy-1,5-imino-(N-ω-methyl caproate]-L-fucitol. These compounds are prepared in a short synthesis from the known compound 2,3-O-­isopropylidene-D-lyxono-1,4-lactone or in a multi-step synthesis from D-galactose.

  本研究提供了用于化学合成 N-取代型 1,5-二脱氧-1,5-亚氨基-L-岩藻糖醇衍生物的新型中间体和方法。一种优选的中间体是 1,5-二脱氧-1,5-亚氨基-3, 4-O-异亚丙基-L-岩藻糖醇，它可用于制备 HIV 抑制剂 1,5-二脱氧-1,5-亚氨基-(N-ω-甲基己酸酯)-L-岩藻糖醇。这些化合物是由已知化合物 2,3-O-异亚丙基-D-来苏诺-1,4-内酯通过简短合成法或由 D-半乳糖通过多步合成法制备的。
• Human iNKT cell activation using glycolipids with altered glycosyl groups
  申请人：Academia Sinica

  公开号：US10918714B2

  公开（公告）日：2021-02-16

  Glycosphingolipids (GSLs) bearing α-glucose (α-Glc) that preferentially stimulate human invariant NKT (iNKT) cells are provided. GSLs with α-glucose (α-Glc) that exhibit stronger induction in humans (but weaker in mice) of cytokines and chemokines and expansion and/or activation of immune cells than those with α-galactose (α-Gal) are disclosed. GSLs bearing α-glucose (α-Glc) and derivatives of α-Glc with F at the 4 and/or 6 positions are provided. Methods for iNKT-independent induction of chemokines by the GSL with α-Glc and derivatives thereof are disclosed. Methods for immune stimulation in humans using GSLs with α-Glc and derivatives thereof are provided.

  本研究提供了能优先刺激人类不变NKT（iNKT）细胞的含有α-葡萄糖（α-Glc）的糖磷脂（GSL）。与含有 α-半乳糖 (α-Gal)的 GSL 相比，含有 α-葡萄糖 (α-Glc)的 GSL 对细胞因子和趋化因子以及免疫细胞的扩增和/或活化的诱导作用更强（但对小鼠的诱导作用较弱）。提供了含有 α-葡萄糖（α-Glc）的 GSL 以及在 4 和/或 6 位上含有 F 的 α-Glc 衍生物。公开了 GSL 与 α-Glc 及其衍生物共同诱导趋化因子而不依赖于 iNKT 的方法。提供了使用含 α-Glc 的 GSL 及其衍生物刺激人体免疫的方法。
• HUMAN iNKT CELL ACTIVATION USING GLYCOLIPIDS WITH ALTERED GLYCOSYL GROUPS
  申请人：Academia Sinica

  公开号：US20190099486A1

  公开（公告）日：2019-04-04

  Glycosphingolipids (GSLs) bearing α-glucose (α-Glc) that preferentially stimulate human invariant NKT (iNKT) cells are provided. GSLs with α-glucose (α-Glc) that exhibit stronger induction in humans (but weaker in mice) of cytokines and chemokines and expansion and/or activation of immune cells than those with α-galactose (α-Gal) are disclosed. GSLs bearing α-glucose (α-Glc) and derivatives of α-Glc with F at the 4 and/or 6 positions are provided. Methods for iNKT-independent induction of chemokines by the GSL with α-Glc and derivatives thereof are disclosed. Methods for immune stimulation in humans using GSLs with α-Glc and derivatives thereof are provided.