p-nitrophenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranoside | 1344980-52-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranoside
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)][TBDPS(-6)]Glc(b)-O-Ph(4-NO2)；[(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-(4-nitrophenoxy)oxan-3-yl] benzoate
• CAS: 1344980-52-4
• 化学式: C₄₉H₄₅NO₁₁Si
• 分子量: 851.982
• InChiKey: UMBPKQPQRALSED-PDWSXWATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.95
• 重原子数：
  62
• 可旋转键数：
  17
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranoside 在 perchloric acid on silica gel 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以90%的产率得到p-nitrophenyl 2,3,4-tri-O-benzoyl-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
• 作为产物：
  描述：

  4-硝基苯-Β-D-吡喃葡萄糖苷 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 作用下， 生成 p-nitrophenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldiphenylsilyl-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。