(Z)-N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2R,3S,4R,5R,6S)-5-acetamido-6-[tert-butyl(dimethyl)silyl]oxy-2-[[(2R,3S,4R,5S,6S)-4,5-dihydroxy-3-methoxy-6-methyloxan-2-yl]oxymethyl]-4-hydroxyoxan-3-yl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxyoxan-3-yl]oxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-4,5-dihydroxyoxan-3-yl]octadec-11-enamide | 182003-45-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2R,3S,4R,5R,6S)-5-acetamido-6-[tert-butyl(dimethyl)silyl]oxy-2-[[(2R,3S,4R,5S,6S)-4,5-dihydroxy-3-methoxy-6-methyloxan-2-yl]oxymethyl]-4-hydroxyoxan-3-yl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxyoxan-3-yl]oxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-4,5-dihydroxyoxan-3-yl]octadec-11-enamide
• CAS: 182003-45-8
• 化学式: C₆₅H₁₂₅N₃O₂₀Si₃
• 分子量: 1352.97
• InChiKey: UEKFGUICTDPBFA-ZUUMHPJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.47
• 重原子数：
  91
• 可旋转键数：
  37
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  310
• 氢给体数：
  9
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  (Z)-N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2R,3S,4R,5R,6S)-5-acetamido-6-[tert-butyl(dimethyl)silyl]oxy-2-[[(2R,3S,4R,5S,6S)-4,5-dihydroxy-3-methoxy-6-methyloxan-2-yl]oxymethyl]-4-hydroxyoxan-3-yl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxyoxan-3-yl]oxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-4,5-dihydroxyoxan-3-yl]octadec-11-enamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 为溶剂， 反应 6.0h， 以83%的产率得到O-[2-deoxy-2-(11(Z)-octadecenamido)-β-D-glucopyranosyl]-(1-4)-(2-acetamido-2-deoxy-2-β-D-glucopyranosyl)-(1-4)-[(2-O-methyl-α-L-fucopyranosyl)-(1-6)]-2-acetamido-2-deoxy-D-glucopyranose
  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：

  乙酸酐 、 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以80%的产率得到(Z)-N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2R,3S,4R,5R,6S)-5-acetamido-6-[tert-butyl(dimethyl)silyl]oxy-2-[[(2R,3S,4R,5S,6S)-4,5-dihydroxy-3-methoxy-6-methyloxan-2-yl]oxymethyl]-4-hydroxyoxan-3-yl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxyoxan-3-yl]oxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-4,5-dihydroxyoxan-3-yl]octadec-11-enamide
  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

文献信息

• 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