phenyl 6-O-[(tert-butyl)diphenylsilyl]-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside | 316188-12-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 6-O-[(tert-butyl)diphenylsilyl]-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside
• CAS: 316188-12-2
• 化学式: C₃₁H₃₈O₅SSi
• 分子量: 550.791
• InChiKey: KXWKAUBGGGPLRN-MJXUZWQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  38.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  phenyl 6-O-[(tert-butyl)diphenylsilyl]-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside 在 四丁基氟化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 phenyl 4,6-di-O-benzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  摘要：

  A series of prearranged glycosides 5, 17, 23, 28, 37 and 41, having a benzyl-protected 1-thiomannosyl donor linked through its positions 2, 3, 4 and 6 via succinate and malonate tethers, respectively, to positions 2, 3, and 6 of a benzyl glucopyranoside acceptor, were prepared by condensation of the respective mannosyl succinates and malonates with suitably protected benzyl glucopyranosides. The prearranged glycosides were intramolecularly coupled under various conditions to give the corresponding, tethered (1 --> 4)-linked disaccharides The yields and anomer ratios of the products of these couplings were interpreted in terms of the thermodynamic stability of the resulting disaccharides. In the case of prearranged glycoside 17, having positions 3 of both the donor and the acceptor linked by a succinate tether, a strong dependence of the diastereoselectivity of the intramolecular glycosylation on the activation procedure was observed. All other cases did not show a significant dependence of the outcome of the anomeric configuration in intramolecular glycosylation on the activation procedure or the solvent.

  DOI：

  10.1002/1522-2675(20001004)83:10<2655::aid-hlca2655>3.0.co;2-u
• 作为产物：
  描述：

  苯基1-硫代吡喃己糖苷 在 咪唑 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 phenyl 6-O-[(tert-butyl)diphenylsilyl]-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  摘要：

  A series of prearranged glycosides 5, 17, 23, 28, 37 and 41, having a benzyl-protected 1-thiomannosyl donor linked through its positions 2, 3, 4 and 6 via succinate and malonate tethers, respectively, to positions 2, 3, and 6 of a benzyl glucopyranoside acceptor, were prepared by condensation of the respective mannosyl succinates and malonates with suitably protected benzyl glucopyranosides. The prearranged glycosides were intramolecularly coupled under various conditions to give the corresponding, tethered (1 --> 4)-linked disaccharides The yields and anomer ratios of the products of these couplings were interpreted in terms of the thermodynamic stability of the resulting disaccharides. In the case of prearranged glycoside 17, having positions 3 of both the donor and the acceptor linked by a succinate tether, a strong dependence of the diastereoselectivity of the intramolecular glycosylation on the activation procedure was observed. All other cases did not show a significant dependence of the outcome of the anomeric configuration in intramolecular glycosylation on the activation procedure or the solvent.

  DOI：

  10.1002/1522-2675(20001004)83:10<2655::aid-hlca2655>3.0.co;2-u

文献信息

• Synthesis of a Glycosylphosphatidylinositol Anchor Derived from <i>Leishmania donovani</i> That Can Be Functionalized by Cu-Catalyzed Azide–Alkyne Cycloadditions
  作者：Ning Ding、Xiuru Li、Zoeisha S. Chinoy、Geert-Jan Boons

  DOI：10.1021/acs.orglett.7b01703

  日期：2017.7.21

  This strategy is based on the use of the 2-naphthylmethyl (Nap) ethers and levulinoyl (Lev) ester for permanent protection of hydroxyls. Removal of seven Nap ethers by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone made it possible to prepare GPIs having an alkyne functionality that could be modified by Cu(I)-catalyzed [3 + 2] cycloadditions to install tags for imaging studies.

  已经开发了一种灵活的组装策略，用于合成带有可点击炔烃标记的利什曼原虫多巴尼GPI锚。此策略基于使用2-萘甲基（Nap）醚和乙酰丙酰基（Lev）酯来永久保护羟基。通过2,3-二氯-5,6-二氰基-1,4-苯醌除去7种Nap醚使得制备具有炔官能度的GPI成为可能，该炔基官能度可通过Cu（I）催化的[3 + 2]环加成反应进行修饰安装用于影像学研究的标签。