4-oxobutyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 146530-07-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-oxobutyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: But-4-al-1-yl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside；3-formylpropyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(4-oxobutoxy)oxan-2-yl]methyl acetate
• CAS: 146530-07-6
• 化学式: C₁₈H₂₆O₁₁
• 分子量: 418.398
• InChiKey: LUGJQJGRLPDGDL-UYTYNIKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  29
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-oxobutyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以85%的产率得到(4-Hydroxy-but-1-yl)-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a symmetric multivalent molecule containing four carbohydrate substituents

  摘要：

  Starting with allyl- and pent-4-enyl-beta-D-glucopyranosides 4-7, different D-Glucose units (8-15) containing alkyl spacers of variable lenght and with different end groups can be prepared. Reaction of four equivalents of the caesium salt derived from propan-4-carboxy-1-yl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside 15 with pentaerythrityltetrabromide yields the tetravalent molecule 16.

  DOI：

  10.1007/bf00811012
• 作为产物：
  描述：

  β-D-葡萄糖五乙酸酯 在 四氯化锡 、 臭氧 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 4-oxobutyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a symmetric multivalent molecule containing four carbohydrate substituents

  摘要：

  Starting with allyl- and pent-4-enyl-beta-D-glucopyranosides 4-7, different D-Glucose units (8-15) containing alkyl spacers of variable lenght and with different end groups can be prepared. Reaction of four equivalents of the caesium salt derived from propan-4-carboxy-1-yl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside 15 with pentaerythrityltetrabromide yields the tetravalent molecule 16.

  DOI：

  10.1007/bf00811012

文献信息

• Organocatalytic and Scalable Syntheses of Unsymmetrical 1,2,4,5‐Tetrazines by Thiol‐Containing Promotors
  作者：Wuyu Mao、Wei Shi、Jie Li、Dunyan Su、Xiaomeng Wang、Lyuye Zhang、Lili Pan、Xiaoai Wu、Haoxing Wu

  DOI：10.1002/anie.201812550

  日期：2019.1.21

  growing application of tetrazine bioorthogonal chemistry, it is still challenging to access tetrazines conveniently from easily available materials. Described here is the de novo formation of tetrazine from nitriles and hydrazine hydrate using a broad array of thiol‐containing catalysts, including peptides. Using this facile methodology, the syntheses of 14 unsymmetric tetrazines, containing a range of

  尽管四嗪生物正交化学的应用不断增长，但仍然难以从易于获得的材料中方便地获得四嗪。此处描述的是使用多种含硫醇的催化剂（包括肽）从腈和水合肼从头形成四嗪。使用这种简便的方法，可以以令人满意的产率实现克级的14种不对称四嗪的合成，其中含有一定范围的反应性官能团。以甲基膦酸四嗪为基础，开发了一种高效的霍纳-沃兹沃思-埃蒙斯反应，可在温和的反应条件下进一步衍生化。具有多种功能的Tetrazine探针可按比例生产，产率为87–93％。
• Use of <i>n</i>-Pentenyl Glycosides as Precursors to Various Spacer Functionalities
  作者：Therese Buskas、Eva Söderberg、Peter Konradsson、Bert Fraser-Reid

  DOI：10.1021/jo9909554

  日期：2000.2.1

  Pent-4-enyl beta-D-glucopyranoside and its peracetylated and perbenzylated derivatives are shown to be excellent substrates for preparation of a wide variety of spacer functionalities. The spacer derivatives so obtained are promising substrates for preparing agents such as neo-glycoconjugates, micelles, and liquid crystalline phases, which are of interest for studying various biological and physiological phenomena of carbohydrates.
• Ferrier, Robert J.; Hall, David W., Journal of the Chemical Society. Perkin transactions I, 1992, # 22, p. 3029 - 3034
  作者：Ferrier, Robert J.、Hall, David W.

  DOI：——

  日期：——