p-methoxyphenyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside | 1344980-53-5

• 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-tri-O-benzyl-α-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-6-(4-methoxyphenoxy)-3,4,5-tris(phenylmethoxy)oxan-2-yl]methanol
• CAS: 1344980-53-5
• 化学式: C₃₄H₃₆O₇
• 分子量: 556.656
• InChiKey: WNPZBHFSUQAYQA-YODGASFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside 在 silica-supported perchloric acid 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以85%的产率得到2,3,4-三(苄氧基)-6,8-二氧杂双环[3.2.1]辛烷
  参考文献：
  名称：

  二氧化硅负载的高氯酸催化合成1,6-脱水糖

  摘要：

  描述了使用二氧化硅负载的高氯酸作为催化剂制备1，6-脱水糖的新的有效方法。该催化剂是非均相的，并且可以在几分钟内以良好的产率形成1，6-脱水糖。

  DOI：

  10.1016/j.tetlet.2011.09.055
• 作为产物：
  描述：

  p-methoxyphenyl 2,3,4-tri-O-benzyl-6-O-triethyl-silyl-α-D-galactopyranoside 在 四丁基氟化铵 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 p-methoxyphenyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside
  参考文献：
  名称：

  Highly Efficient and Mild Method for Regioselective De-O-benzylation of Saccharides by Co₂(CO)₈-Et₃SiH−CO Reagent System

  摘要：

  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%).

  DOI：

  10.1021/ol902717y

文献信息

• An efficient and recyclable catalyst for the cleavage of tert-butyldiphenylsilyl ethers
  作者：Shiqiang Yan、Ning Ding、Wei Zhang、Peng Wang、Yingxia Li、Ming Li

  DOI：10.1016/j.carres.2012.02.021

  日期：2012.6

  An efficient, chemoselective, and environment-friendly method for the deprotection of tert-butyldiphenylsilyl ethers mediated by triflic acid supported on silica gel is reported. A wide range of tert-butyldiphenylsilyl ethers derived from carbohydrate and saponin residues can be smoothly cleaved in the presence of various types of other protecting groups in good to excellent yields in acetonitrile. This heterogeneous reaction does not require aqueous workup, and the supported catalyst can be readily recycled. (C) 2012 Elsevier Ltd. All rights reserved.
• Efficient Synthesis of the Pentasaccharide Repeating Unit of the O-Antigenic Polysaccharide of Escherichia coli O166 Strain
  作者：Anup Misra、Anshupriya Si

  DOI：10.1055/s-0034-1378911

  日期：——

  An efficient strategy has been developed for the synthesis of the pentasaccharide repeating unit of the cell-wall polysaccharide of Escherichia coli O166 strain through sequential stereoselective glycosylations of monosaccharide intermediates. All the glycosylation steps were high-yielding with high stereoselectivities.
• 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%).
• Synthesis of 1,6-anhydro sugars catalyzed by silica supported perchloric acid
  作者：Yuexing Chun、Shiqiang Yan、Xiangpeng Li、Ning Ding、Wei Zhang、Peng Wang、Ming Li、Yingxia Li

  DOI：10.1016/j.tetlet.2011.09.055

  日期：2011.11

  A new and efficient method for the preparation of 1,6-anhydro sugars using silica supported perchloric acid as a catalyst is described. The catalyst is heterogeneous and 1,6-anhydro sugars could be formed within a few minutes with good yields.

  描述了使用二氧化硅负载的高氯酸作为催化剂制备1，6-脱水糖的新的有效方法。该催化剂是非均相的，并且可以在几分钟内以良好的产率形成1，6-脱水糖。