(pent-4′-enyl) 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside | 117841-64-2

• 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: (pent-4′-enyl) 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside
• 英文别名: n-pent-4-enyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside；n-pentenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside；(2S,3S,4S,5R,6R)-2-pent-4-enoxy-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 117841-64-2
• 化学式: C₃₉H₄₄O₆
• 分子量: 608.775
• InChiKey: UJKZBFGKKCLGDY-QRBPUMSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  45
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (pent-4′-enyl) 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 在 tetrafluoroboric acid 、 bis(pyridine)iodonium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以94%的产率得到2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl fluoride
  参考文献：
  名称：

  IPy2BF4介导的正戊烯基糖苷向糖基氟化物的转化：一对新的半正交糖基供体。

  摘要：

  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。

  DOI：

  10.1021/ol070753r
• 作为产物：
  描述：

  4-pentenyl 2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 sodium methylate 作用下， 生成 (pent-4′-enyl) 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of a key Mycobacterium tuberculosis biosynthetic phosphoinositide intermediate

  摘要：

  Regioselective mannosylations of a myoinositol acceptor diol are readily achieved by Lewis acid mediated iodinolysis of n-pentenyl ortho-esters. The procedure affords a psuedotrisaccharide to which the phosphoglyceryl and other lipid residues are added leading to the key biosynthetic intermediate of Mycobacterium species. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.103

文献信息

• Methyl glycosides are identified as glycosyl donors for the synthesis of glycosides, disaccharides and oligosaccharides
  作者：Srinivasa Rao Vidadala、Srinivas Hotha

  DOI：10.1039/b822526e

  日期：——

  Stable methyl glycosides are identified as glycosyl donors in the presence of AuBr(3) in acetonitrile; a panel of aglycones comprising aliphatic, alicyclic, steroidal and sugar alcohols are examined successfully for the glycosylation reaction and methyl glycosides of di- and tri- saccharides are converted to corresponding tri- and tetra-saccharides exploiting salient features of our novel activation

  在乙腈中存在AuBr（3）的情况下，稳定的甲基糖苷被鉴定为糖基供体；利用我们新颖的激活方案的显着特征，成功地检测了一组包含脂肪族，脂环族，甾族和糖醇的糖苷配基的糖基化反应，并将二糖和三糖的甲基糖苷转化为相应的三糖和四糖。
• 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。
• Stereocontrolled glycoside synthesis by activation of glycosyl sulfone donors with scandium(<scp>iii</scp>) triflate
  作者：Amandine Xolin、Romain Losa、Aicha Kaid、Cédric Tresse、Jean-Marie Beau、François-Didier Boyer、Stéphanie Norsikian

  DOI：10.1039/c7ob02792c

  日期：——

  The activation of aryl glycosyl sulfone donors has been achieved using scandium(III) triflate and has led to the selective preparation of α-mannosides resulting from a post-glycosylation anomerization.

  使用三氟甲磺酸scan （III）已经实现了芳基糖基砜供体的活化，并导致了由糖基化后的异构化反应产生的α-甘露糖苷的选择性制备。
• Preparation, Properties, and Applications of <i>n</i>-Pentenyl Arabinofuranosyl Donors
  作者：Jun Lu、Bert Fraser-Reid

  DOI：10.1021/ol0490680

  日期：2004.9.1

  development of n-pentenyl furanosyl donors has been tested using arabinose as a model. The readily prepared ortho ester (NPOE) is converted into disarmed (NPG(AC)) and thence armed (NPG(ALK)) n-pentenyl arabinofuranosides. The reactivities of these furanosyl donors and pyranosyl counterparts have been assessed by allowing pairs of both to compete for an acceptor. For the NPOE and armed (NPG(ALK)) pairs

  [反应：见正文]已使用阿拉伯糖作为模型测试了正戊烯基呋喃糖基供体的发育。易于制备的原酸酯（NPOE）被转化为脱甲（NPG（ACK）），然后被武装（NPG（ALK））正戊烯基阿拉伯呋喃糖苷。这些呋喃糖基供体和吡喃糖基对应物的反应性已经通过允许两者成对竞争竞争受体来评估。对于NPOE和武装（NPG（ALK））对，从供体中获得偶联产物，而对于解除武装（NPG（AC））对，仅获得阿拉伯呋喃诺偶联产物。为了探究其合成用途，已证明NPOE是制备结核分枝杆菌复杂lipoarabinomannan细胞壁阵列的α-1,5-连接的阿拉伯聚糖片段所需的唯一前体。
• 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。