pent-4-enyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside | 182003-00-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pent-4-enyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside
• 英文别名: [(2R,3R,4R,5S,6R)-5-hydroxy-2-pent-4-enoxy-6-(phenylmethoxymethyl)-3-(4,5,6,7-tetrachloro-1,3-dioxoisoindol-2-yl)oxan-4-yl] acetate
• CAS: 182003-00-5
• 化学式: C₂₈H₂₇Cl₄NO₈
• 分子量: 647.336
• InChiKey: MYBHHIBKUORUDJ-KWHOMZPESA-N

物化性质

• 沸点：
  733.238±60.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.499±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  pent-4-enyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 三乙基硅基三氟甲磺酸酯 、 sodium iodide 作用下， 以 二氯甲烷 、 丁酮 为溶剂， 反应 15.27h， 生成 pent-4-enyl (3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranosyl)-(1-4)-3-O-acetyl-6-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：

  2-脱氧-2-(四氯苯二甲酰亚胺基)-D-吡喃葡萄糖-1,3,4,6-四乙酸盐 生成 pent-4-enyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  结瘤因子：通过NodRf-III（C18：1）（MeFuc）的总合成说明的后期关键中间体的汇聚策略。

  摘要：

  DOI：

  10.1021/jo961115h

文献信息

• Bromination of Alkenyl Glycosides with Copper(II) Bromide and Lithium Bromide:  Synthesis, Mechanism, and DFT Calculations
  作者：Robert Rodebaugh、John S. Debenham、Bert Fraser-Reid、James P. Snyder

  DOI：10.1021/jo9718509

  日期：1999.3.1