1-O-(4-pentenyl)-L-fucopyranoside | 676518-71-1

• 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: 1-O-(4-pentenyl)-L-fucopyranoside
• CAS: 676518-71-1
• 化学式: C₁₁H₂₀O₅
• 分子量: 232.277
• InChiKey: MCCANGQJXWVIBN-SEBBVZKISA-N

物化性质

• 沸点：
  370.2±42.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  79.15
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-O-(4-pentenyl)-L-fucopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 三乙基硅基三氟甲磺酸酯 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 5.92h， 生成 benzyl (3,4-di-O-benzoyl-2-O-methyl-α-L-fucopyranosyl)-(1-6)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  TCP- and Phthalimide-Protected n-Pentenyl Glucosaminide Precursors for the Synthesis of Nodulation Factors As Illustrated by the Total Synthesis of NodRf-III (C18:1, MeFuc)

  摘要：

  TCP- and phthalimide-protected n-pentenyl glucosaminide (NPG) precursors have been utilized in a convergent stereocontrolled synthesis of the nodulation factor NodRf-III (C18:1, MeFuc) produced by Rhizobium fredii USDA257, 2. Nodulation factors are lipooligosaccharides that are secreted by bacteria which trigger the early steps in the formation of root nodules in leguminous plants. This symbiotic relationship between plant and bacteria plays a major role in the global nitrogen cycle. Key to our synthetic approach was the use of the TCP (tetrachlorophthaloyl) group to provide for N-differentiation of the linear glucosamine backbone and the use of FeCl3 for the removal of benzyl protecting groups from the tetrasaccharide. The saccharide skeleton was assembled via the NPG-based coupling of a linear beta(1-->4) glucosamine disaccharide to a 6-O-fucosylated glucosamine acceptor. Significant yield enhancements for NPG couplings were observed at lower temperatures. Subsequent exchange of benzyl to tert-butyldimethylsilyl protecting groups via FeCl3 mediation and installation of the fatty chain on the nonreducing terminus via selective removal of TCP led to a late intermediate which was deprotected in high yield to afford the natural product.

  DOI：

  10.1021/jo962362o
• 作为产物：
  描述：

  4-戊烯-1-醇 、 6-deoxy-L-galactose 在 D(+)-10-樟脑磺酸 作用下， 以71%的产率得到1-O-(4-pentenyl)-L-fucopyranoside
  参考文献：
  名称：

  Design and Synthesis of Peptide Mimetics of GDP-Fucose: Targeting Inhibitors of Fucosyltransferases

  摘要：

  基于UDP-N-乙酰葡糖胺的多肽模拟物尼克霉素Z对N-乙酰葡糖胺转移酶具有强效抑制活性的背景，我们设计并合成了新型的GDP-岩藻糖多肽模拟物，其目标是抑制从GDP-岩藻糖转移l-岩藻糖至寡糖的岩藻糖转移酶。GDP-岩藻糖模拟物的合成路线是利用 l-苏氨酸醛缩酶催化的酶促醛缩反应来制备携带δ-²-羟基-δ±-l-氨基酸的鸟嘌呤，这是一种关键的合成中间体。

  DOI：

  10.1055/s-2003-44984

文献信息

• n-pentenyl glycosides in the efficient assembly of the blood group substance B tetrasaccharide
  作者：Uko E. Udodong、C. Srinivas Rao、Bert Fraser-Reid

  DOI：10.1016/s0040-4020(01)81568-4

  日期：1992.6

  monosaccharide components of the human blood-group determinant B are prepared with full or partial protection as required. Assembly of the tetrasaccharide then requires only five steps, three to give, in sequence, the disaccharide (68%), trisaccharide (82%), and tetrasaccharide (91%), the other two steps being required to deprotect hydroxyl groups at the di- and tri-saccharide levels for the ensuing

  正戊烯基糖苷（nPG）对多种反应条件稳定，但仍可以被化学特异性活化的事实，对于寡糖的高效，收敛组装是有利的。nPG可直接从醛糖或通过正常的糖苷形成反应制备，并通过使用N-碘代琥珀酰亚胺/三乙基甲硅烷基三氟甲磺酸盐作为碘鎓源，甚至“解除武装”的糖基供体也会在数分钟内反应。人血型决定簇B的四种单糖组分可根据需要进行全部或部分保护。这样，四糖的组装仅需五个步骤，三个步骤依次得到二糖（68％），三糖（82％）和四糖（91％），
• Nodulation Factors:  A Strategy for Convergent Assembly of a Late-Stage Key Intermediate Illustrated by the Total Synthesis of NodRf-III (C18:1) (MeFuc)
  作者：John S. Debenham、Robert Rodebaugh、Bert Fraser-Reid

  DOI：10.1021/jo961115h

  日期：1996.1.1