(((3aR,4R,6R,6aR)-6-bromo-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)(tert-butyl)diphenylsilane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (((3aR,4R,6R,6aR)-6-bromo-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)(tert-butyl)diphenylsilane
• 英文别名: [(3aR,4R,6R,6aR)-4-bromo-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy-tert-butyl-diphenylsilane
• 化学式: C₂₄H₃₁BrO₄Si
• 分子量: 491.497
• InChiKey: DFIFGPOKVJDUQL-YSFYHYPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (((3aR,4R,6R,6aR)-6-bromo-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)(tert-butyl)diphenylsilane 在 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  “Boomerang” Strategy in Carbohydrate Chemistry: Diastereoselective Synthesis of C-Glycosylated Benzothiazoles from ortho-Isocyanophenyl Thioglycosides

  摘要：

  DOI：

  10.1021/acs.orglett.3c03817
• 作为产物：
  描述：

  5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以52%的产率得到(((3aR,4R,6R,6aR)-6-bromo-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)(tert-butyl)diphenylsilane
  参考文献：
  名称：

  Cobalt-Catalyzed Diastereoselective Synthesis of C-Furanosides. Total Synthesis of (−)-Isoaltholactone

  摘要：

  An array of C-aryl and C-vinyl furanosides were prepared in good yields and diastereoselectivities from C-halogeno furanosides either with aryl Grignard or with vinyl Grignard using the convenient Co(acac)(3)/TMEDA catalytic system. This method is illustrated by the total synthesis of the (-)-isoaltholactone.

  DOI：

  10.1021/jo401845q

文献信息

• Direct Formation of Amide-Linked <i>C</i>-Glycosyl Amino Acids and Peptides via Photoredox/Nickel Dual Catalysis
  作者：Xiang-Yu Ye、Guanjie Wang、Zhichao Jin、Bin Yu、Junmin Zhang、Shichao Ren、Yonggui Robin Chi

  DOI：10.1021/jacs.3c13456

  日期：2024.2.28

  Our amide-linked C-glycosyl amino acids and peptides are synthesized through cooperative Ni-catalyzed and photoredox processes. The catalytic process generates a glycosyl radical and an amide carbonyl radical, which subsequently combine to yield the C-glycosyl products. The saccharide reaction partners encompass mono-, di-, and trisaccharides. All 20 natural amino acids, peptides, and their derivatives

  糖蛋白负责许多生物过程，包括与疾病和感染相关的生物过程。糖肽的进步已成为解开生物途径和发现新药物的有前途的策略。在这个领域，一个关键的挑战是缺乏有效的合成策略来获取糖肽和糖蛋白。在这里，我们提出了一种通过酰胺键将糖与氨基酸和肽桥接的高度简洁的方法。我们的酰胺连接C-糖基氨基酸和肽是通过镍催化和光氧化还原过程协同合成的。催化过程产生糖基自由基和酰胺羰基自由基，它们随后结合产生C-糖基产物。糖反应伴侣包括单糖、二糖和三糖。所有 20 种天然氨基酸、肽及其衍生物都可以有效地进行糖基化，产率从可接受到高不等，表现出优异的立体选择性。作为应用的实质性扩展，我们已经证明简单的C-糖基氨基酸可以作为通用的构建单元来构建具有复杂空间复杂性的C-糖肽。
• Triphenylphosphine: a catalyst for the synthesis of C-aryl furanosides from furanosyl halides
  作者：Lionel Nicolas、Patrick Angibaud、Ian Stansfield、Lieven Meerpoel、Sébastien Reymond、Janine Cossy

  DOI：10.1016/j.tetlet.2013.12.035

  日期：2014.1

  An array of C-aryl furanosides was prepared in good yields from furanosyl halides and aryl Grignard reagents in Et2O using PPh3 as a catalyst. (C) 2013 Elsevier Ltd. All rights reserved.
• Cobalt-Catalyzed Diastereoselective Synthesis of <i>C</i>-Furanosides. Total Synthesis of (−)-Isoaltholactone
  作者：Lionel Nicolas、Eva Izquierdo、Patrick Angibaud、Ian Stansfield、Lieven Meerpoel、Sébastien Reymond、Janine Cossy

  DOI：10.1021/jo401845q

  日期：2013.12.6

  An array of C-aryl and C-vinyl furanosides were prepared in good yields and diastereoselectivities from C-halogeno furanosides either with aryl Grignard or with vinyl Grignard using the convenient Co(acac)(3)/TMEDA catalytic system. This method is illustrated by the total synthesis of the (-)-isoaltholactone.
• “Boomerang” Strategy in Carbohydrate Chemistry: Diastereoselective Synthesis of <i>C</i>-Glycosylated Benzothiazoles from <i>ortho</i>-Isocyanophenyl Thioglycosides
  作者：Li-Yan Hu、Shen-Yuan Zhang、Li Zhu、Yang Li、Kai Luo、Lei Wu

  DOI：10.1021/acs.orglett.3c03817

  日期：2024.1.12