benzyl 6-O-allyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside | 1492828-97-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 6-O-allyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2,3,4,5-tetrakis(phenylmethoxy)-6-(prop-2-enoxymethyl)oxane
• CAS: 1492828-97-3
• 化学式: C₃₇H₄₀O₆
• 分子量: 580.721
• InChiKey: RYFTVFTVRDVTOO-KHKVHWIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,2,3,4-四苄基-beta-d-吡喃葡萄糖 、 allyl 2,2,2-trifluoro-N-(4-nitrophenyl)acetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 以81%的产率得到benzyl 6-O-allyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  The development of N-aryl trifluoroacetimidate-based benzyl and allyl protecting group reagents

  摘要：

  An exploration of the role of para-substituents on the balance between stability and reactivity of N-phenyl trifluoroacetimidates prompted the discovery of new reagents for the addition of allyl and benzyl protecting groups, namely O-allyl and O-benzyl N-(p-nitrophenyl)trifluoroimidates. These compounds are stable and crystalline at ambient temperature, making them ideal alternatives to existing benzylating and allylating reagents used under acidic conditions. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.014

文献信息

• The development of N-aryl trifluoroacetimidate-based benzyl and allyl protecting group reagents
  作者：Sinele B. Tsabedze、Daniel E.K. Kabotso、Nicola L.B. Pohl

  DOI：10.1016/j.tetlet.2013.09.014

  日期：2013.12

  An exploration of the role of para-substituents on the balance between stability and reactivity of N-phenyl trifluoroacetimidates prompted the discovery of new reagents for the addition of allyl and benzyl protecting groups, namely O-allyl and O-benzyl N-(p-nitrophenyl)trifluoroimidates. These compounds are stable and crystalline at ambient temperature, making them ideal alternatives to existing benzylating and allylating reagents used under acidic conditions. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.