n-pent-4-enyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside | 125367-09-1

• 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: n-pent-4-enyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside
• 英文别名: 4-pentenyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside；n-pentenyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside；[(2R,3R,4S,5S,6S)-3,4,5-tribenzoyloxy-6-pent-4-enoxyoxan-2-yl]methyl benzoate
• CAS: 125367-09-1；125367-10-4；143416-41-5；128503-34-4
• 化学式: C₃₉H₃₆O₁₀
• 分子量: 664.709
• InChiKey: FBMVGHGZTJNDOJ-DPSJXZRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  49
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  n-pent-4-enyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 在 Grubbs catalyst first generation 、 N-碘代丁二酰亚胺 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 12.17h， 生成 [9-O-tert-butyldiphenylsilyl-4-nonenyl]6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Ready access to a branched Man5 oligosaccharide based on regioselective glycosylations of a mannose-tetraol with n-pentenyl orthoesters

  摘要：

  一种分支的Man5寡糖通过在氯仿中使用NIS/BF3·Et2O促进的n-戊烯基正交酯糖苷供体对甘露糖四醇进行顺序区域选择性糖苷化反应合成。为了便于（a）起始四醇在氯仿中的溶解度，以及（b）将来对Man5寡糖还原末端的操作，将一个延伸的n-戊烯基链引入了四醇受体中。

  DOI：

  10.1039/c2ob26432c
• 作为产物：
  描述：

  D-甘露糖 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 甲胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 n-pent-4-enyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  Cross Metathesis Assisted Solid-Phase Synthesis of Glycopeptoids

  摘要：

  A solid-phase synthesis of glycopeptoids was explored through olefin cross metathesis (CM). Peptoids and sugar derivatives with appropriate olefin moieties were coupled in the presence of an olefin metathesis catalyst to afford glycopeptoids in good yields. This systematic solid-phase CM study can provide facile access to the molecular sources of glycopeptidomimetics and postchemical modifications on various molecular scaffolds.

  DOI：

  10.1021/ol300808c

文献信息

• Iodonium ion generated in situ from N-iodosuccinimide and trifluoromethanesulphonic acid promotes direct linkage of ‘disarmed’ pent-4-enyl glycosides
  作者：Peter Konradsson、David R. Mootoo、Robert E. McDevitt、Bert Fraser-Reid

  DOI：10.1039/c39900000270

  日期：——

  N-Iodosuccinimide and trifluoromethanesulphonic acid provide a powerful source of Iodonium ion which allows ‘disarmed’ pent-4-enyl glycosides that normally respond sluggishly to lodonium dicollidine perchlorate, to react rapidly and to exhibit stereodirection via neighbouring group participation of C-2 esters.

  N-碘代琥珀酰亚胺和三氟甲磺酸提供了强大的碘离子源，它使通常通常对慢二氯可乐定高氯酸钾反应迟钝的“脱甲”戊-4-烯基糖苷反应迅速，并通过C-2酯的相邻基团参与而表现出立体定向性。
• Glycosyl fluorides from <i>n</i>-pentenyl-related glycosyl donors — Application to glycosylation strategies
  作者：Bert Fraser-Reid、J. Cristobal Lopez、Paloma Bernal-Albert、Ana M. Gomez、Clara Uriel、Juan Ventura

  DOI：10.1139/cjc-2012-0285

  日期：2013.1

  fluorides by a variety of methods. In the case of NPGs, Barluenga’s reagent, bis(pyridinium)iodonium(I)tetrafluoroborate (IPy2BF4), gives good yields of glycosyl fluorides when HF–pyridine complex is used as an additional fluoride source. NPOEs can be activated either by a combination of electrophilic iodonium (Barluenga’s reagent) and HBF4 or by the action of HF–pyridine complex. The ensuing glycosyl

  正戊烯基糖苷 (NPG) 和正戊烯基原酸酯 (NPOE) 已通过多种方法转化为糖基氟。在 NPG 的情况下，当使用 HF-吡啶复合物作为额外的氟化物来源时，Barluenga 试剂双（吡啶鎓）碘鎓（I）四氟硼酸盐（IPy2BF4）可产生良好的糖基氟化物产率。NPOE 可以通过亲电子碘鎓（Barluenga 试剂）和 HBF4 的组合或通过 HF-吡啶复合物的作用被激活。当遇到 NPG 时，随之而来的糖基氟化物会形成一对半正交的糖基供体。
• IPy₂BF₄-Mediated Transformation of <i>n</i>-Pentenyl Glycosides to Glycosyl Fluorides:  A New Pair of Semiorthogonal Glycosyl Donors
  作者：J. Cristóbal López、Clara Uriel、Alejandra Guillamón-Martín、Serafín Valverde、Ana M. Gómez

  DOI：10.1021/ol070753r

  日期：2007.7.1

  Bis(pyridinium) iodonium(I) tetrafluoroborate (IPy2BF4), a solid and stable reagent, can be used to transform n-pentenyl orthoesters (NPOEs) and n-pentenyl glycosides (NPGs) into glycosyl fluorides. The latter pair constitutes a new set of semiorthogonal glycosyl donors that can be used in glycosylation strategies, alone or in combination with NPOEs.

  固态且稳定的试剂双吡啶鎓碘鎓（I）四氟硼酸酯（IPy2BF4）可用于将正戊烯基原酸酯（NPOE）和正戊烯基糖苷（NPG）转化为糖基氟化物。后者构成了一组新的半正交糖基供体，可单独或与NPOE结合用于糖基化策略。
• Propargyl 1,2-orthoesters as glycosyl donors: stereoselective synthesis of 1,2-trans glycosides and disaccharides
  作者：Gopalsamy Sureshkumar、Srinivas Hotha

  DOI：10.1016/j.tetlet.2007.07.015

  日期：2007.9

  Propargyl 1,2-orthoesters are identified as glycosyl donors. Various glycosides and disaccharides were synthesized in a stereoselective manner using AuBr3 as the promoter. AuBr3 may activate the alkyne resulting in the formation of a 1,2-dioxolenium ion and also behaves as a Lewis acid to facilitate the attack of the glycosyl acceptor. The versatility of the protocol was demonstrated using a panel of aglycones comprising aliphatic, alicyclic, steroidal and sugar alcohols. (C) 2007 Elsevier Ltd. All rights reserved.
• KONRADSSON, PETER;MOOTOO, DAVID R.;MCDEVITT, ROBERT E.;FRASER-REID, BERT, J. CHEM. SOC. CHEM. COMMUN.,(1990) N, C. 270-272
  作者：KONRADSSON, PETER、MOOTOO, DAVID R.、MCDEVITT, ROBERT E.、FRASER-REID, BERT

  DOI：——

  日期：——