p-methoxyphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside | 173597-19-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside
• 英文别名: 4-methoxyphenyl-2,3,4,6-tetra-O-benzyl-D-mannopyranoside
• CAS: 173597-19-8
• 化学式: C₄₁H₄₂O₇
• 分子量: 646.78
• InChiKey: QXYYOIDTAHLOQE-HJRBIJKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.77
• 重原子数：
  48.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 以 水 、 乙腈 为溶剂， 反应 4.0h， 以92%的产率得到2,3,4,6-tetra-O-benzyl-D-mannopyranose
  参考文献：
  名称：

  Deprotection of p-methoxyphenyl pyranosides by anodic oxidation

  摘要：

  DOI：

  10.1016/0008-6215(95)00223-g
• 作为产物：
  描述：

  4-甲氧苯基-2,3,4,6-四-O-乙酰基-Alpha-D-吡喃甘露糖苷 在 Dowex 1-X₂ resin (OH-form) 、 sodium hydride 作用下， 以 甲醇 、 水 为溶剂， 反应 26.42h， 生成 p-methoxyphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Deprotection of p-methoxyphenyl pyranosides by anodic oxidation

  摘要：

  DOI：

  10.1016/0008-6215(95)00223-g

文献信息

• Active Cobalt Catalyst for the Cleavage of Benzyl Ether
  作者：Bo Wang、Zhaojun Yin、Yangbing Li、Ting-Xiang Yang、Xiang-Bao Meng、Zhong-Jun Li

  DOI：10.1021/jo2018284

  日期：2011.11.18

  An improved method for the deprotection of benzyl ethers using a catalytic amount of Co2(CO)8 in the presence of Me2PhSiH and CO (1 atm) is described. The deprotection reaction is compatible with double bond or sulfur-containing substrates. The method also tolerates other functional groups, such as Ac, Piv, and Bz, and shows potential selectivity in perbenzylated monosaccharides.

  描述了一种在Me 2 PhSiH和CO（1 atm）存在下使用催化量的Co 2（CO）8脱除苄基醚的改进方法。脱保护反应与双键或含硫底物相容。该方法还可以耐受其他官能团，例如Ac，Piv和Bz，并在过苄基单糖中显示出潜在的选择性。
• Copper-mediated anomeric <i>O</i>-arylation with organoboron reagents
  作者：Victoria Dimakos、Jacklyn J. W. Liu、Zhenlu Ge、Mark S. Taylor

  DOI：10.1039/c9ob01022j

  日期：——

  Copper-mediated couplings of arylboroxines with glycosyl hemiacetals furnish O-aryl glycosides via Csp2-O bond formation. The method enables the anomeric O-arylation of protected pyranose and furanose derivatives, and is tolerant of functionalized arylboroxine partners. Whereas mixtures of anomers are formed from glucopyranose, galactopyranose and arabinofuranose hemiacetals, the α-anomer is generated

  铜介导的芳基硼氧烷与糖基半缩醛的偶联通过Csp2-O键的形成提供了O-芳基糖苷。该方法能够使受保护的吡喃糖和呋喃糖衍生物进行异头O-芳基化，并能耐受官能化的芳基环硼氧烷伴侣。由吡喃葡萄糖，半乳糖吡喃糖和阿拉伯呋喃糖半缩醛形成端基异构体的混合物，而α-端基异构体则是从甘露吡喃糖和甘露呋喃糖衍生的底物中选择性产生的。
• Highly Efficient and Mild Method for Regioselective De-<i>O</i>-benzylation of Saccharides by Co₂(CO)₈-Et₃SiH−CO Reagent System
  作者：Zhao-Jun Yin、Bo Wang、Yang-Bing Li、Xiang-Bao Meng、Zhong-Jun Li

  DOI：10.1021/ol902717y

  日期：2010.2.5

  A highly efficient and mild method for the de-O-benzylation of protected saccharides was developed by transforming terminal benzyl ethers into silyl ethers using Co-2(CO)(8)-Et3SiH under 1 atm of CO. The method was successfully used for the de-O-benzylation of perbenzylated monosaccharides with various anomeric protecting groups, as well as natural disaccharides and trisaccharides such as sucrose, raffinose, and melezitose in good yields (>80%).