3-(((2S,3R,4S,5R)-3,4,5-tris(benzyloxy)tetrahydro-2H-pyran-2-yl)oxy)propan-1-ol | 1310450-10-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(((2S,3R,4S,5R)-3,4,5-tris(benzyloxy)tetrahydro-2H-pyran-2-yl)oxy)propan-1-ol
• 英文别名: 3-[(2S,3R,4S,5R)-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxypropan-1-ol
• CAS: 1310450-10-2
• 化学式: C₂₉H₃₄O₆
• 分子量: 478.585
• InChiKey: LXQJNMHUPGIDRS-AIQXTLEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(dimethylamino)-α,α-diphenylbenzenemethanol 1-acetate 、 3-(((2S,3R,4S,5R)-3,4,5-tris(benzyloxy)tetrahydro-2H-pyran-2-yl)oxy)propan-1-ol 以 甲苯 为溶剂， 反应 3.0h， 以91%的产率得到3-[diphenyl-[3-[(2S,3R,4S,5R)-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxypropoxy]methyl]-N,N-dimethylaniline
  参考文献：
  名称：

  Development of Trityl-Based Photolabile Hydroxyl Protecting Groups

  摘要：

  A series of trityl-based photolabile hydroxyl protecting groups have been examined. These PPGs evolve from the traditional acid-labile trityl protecting group with proper electron-donating substituents. Structure-reactivity relationships have been explored. A m-dimethylamino group is crucial to achieve high photochemical deprotection efficiency. The o-hydroxyl group in 8 greatly improves the yield of the photochemical deprotection reaction, compared with the corresponding o-methoxyl-substituted counterpart 7. However, comparison between the photoreactions of 9 and 11 does not show similar structural relevance. The PPG in ether I (i.e., DMATr group) is structurally simple and easy to prepare and install. Its deprotection can be successfully carried out with irradiation of sunlight without requirement of photochemical devices.

  DOI：

  10.1021/jo200692c
• 作为产物：
  描述：

  allyl 2,3,4-tri-O-benzyl-α-D-xylopyranoside 在 dimethyl sulfide borane 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以81%的产率得到3-(((2S,3R,4S,5R)-3,4,5-tris(benzyloxy)tetrahydro-2H-pyran-2-yl)oxy)propan-1-ol
  参考文献：
  名称：

  Development of Trityl-Based Photolabile Hydroxyl Protecting Groups

  摘要：

  A series of trityl-based photolabile hydroxyl protecting groups have been examined. These PPGs evolve from the traditional acid-labile trityl protecting group with proper electron-donating substituents. Structure-reactivity relationships have been explored. A m-dimethylamino group is crucial to achieve high photochemical deprotection efficiency. The o-hydroxyl group in 8 greatly improves the yield of the photochemical deprotection reaction, compared with the corresponding o-methoxyl-substituted counterpart 7. However, comparison between the photoreactions of 9 and 11 does not show similar structural relevance. The PPG in ether I (i.e., DMATr group) is structurally simple and easy to prepare and install. Its deprotection can be successfully carried out with irradiation of sunlight without requirement of photochemical devices.

  DOI：

  10.1021/jo200692c

文献信息

• Development of Trityl-Based Photolabile Hydroxyl Protecting Groups
  作者：Lei Zhou、Haishen Yang、Pengfei Wang

  DOI：10.1021/jo200692c

  日期：2011.8.5

  A series of trityl-based photolabile hydroxyl protecting groups have been examined. These PPGs evolve from the traditional acid-labile trityl protecting group with proper electron-donating substituents. Structure-reactivity relationships have been explored. A m-dimethylamino group is crucial to achieve high photochemical deprotection efficiency. The o-hydroxyl group in 8 greatly improves the yield of the photochemical deprotection reaction, compared with the corresponding o-methoxyl-substituted counterpart 7. However, comparison between the photoreactions of 9 and 11 does not show similar structural relevance. The PPG in ether I (i.e., DMATr group) is structurally simple and easy to prepare and install. Its deprotection can be successfully carried out with irradiation of sunlight without requirement of photochemical devices.