p-methoxyphenyl 3,4-di-O-benzoyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 1344980-43-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 3,4-di-O-benzoyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-4-benzoyloxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-(1,3-dioxoisoindol-2-yl)-6-(4-methoxyphenoxy)oxan-3-yl] benzoate
• CAS: 1344980-43-3
• 化学式: C₅₁H₄₇NO₁₀Si
• 分子量: 862.02
• InChiKey: CJFFNCPKFKYQFW-ICIYLCIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.49
• 重原子数：
  63
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 3,4-di-O-benzoyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 1,3-二溴-5,5-二甲基海因 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以89%的产率得到p-methoxyphenyl 3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  1,3-二溴-5,5-二甲基乙内酰脲催化裂解叔丁基二苯基甲硅烷基醚的有效方法

  摘要：

  摘要 建立了以1,3-二溴-5,5-二甲基乙内酰脲(DBH)为催化剂、二甲基亚砜(DMSO)为溶剂的叔丁基二苯基甲硅烷基(TBDPS)醚脱保护的有效方法。该方法适用于多种化合物，例如碳水化合物、类固醇、苯甲醇和脂肪伯醇。带有乙酸盐、苯甲酸盐、新戊酸盐、甲磺酸盐和苄基醚和对甲氧基苄基醚的底物是相容的。

  DOI：

  10.1080/07328303.2022.2031206
• 作为产物：
  描述：

  4-methoxyphenyl 2-deoxy-2-phthalimido-β-D-glucopyranoside 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 作用下， 生成 p-methoxyphenyl 3,4-di-O-benzoyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  An efficient and recyclable catalyst for the cleavage of tert-butyldiphenylsilyl ethers

  摘要：

  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.

  DOI：

  10.1016/j.carres.2012.02.021

文献信息

• 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。
• 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.
• An efficient method for the cleavage of <i>tert</i>-butyldiphenylsilyl ethers catalyzed by 1,3-dibromo-5,5-dimethylhydantoin
  作者：Zong Han

  DOI：10.1080/07328303.2022.2031206

  日期：2022.1.2

  Abstract An efficient method for the deprotection of tert-butyldiphenylsilyl (TBDPS) ethers using 1,3-dibromo-5,5-dimethylhydantoin (DBH) as catalyst and dimethyl sulfoxide (DMSO) as solvent has been established. This method is useful for many kinds of compounds, such as carbohydrates, steroids, benzyl alcohols and primary fatty alcohols. Substrates bearing acetates, benzoates, pivaloates, mesylates, and benzyl

  摘要 建立了以1,3-二溴-5,5-二甲基乙内酰脲(DBH)为催化剂、二甲基亚砜(DMSO)为溶剂的叔丁基二苯基甲硅烷基(TBDPS)醚脱保护的有效方法。该方法适用于多种化合物，例如碳水化合物、类固醇、苯甲醇和脂肪伯醇。带有乙酸盐、苯甲酸盐、新戊酸盐、甲磺酸盐和苄基醚和对甲氧基苄基醚的底物是相容的。