[(3S,3'R,4'S,5'S,6'R)-6'-[[tert-butyl(dimethyl)silyl]oxymethyl]-4',5'-dihydroxy-4,6-bis[tri(propan-2-yl)silyloxy]spiro[1H-2-benzofuran-3,2'-oxane]-3'-yl] (E)-3-phenylprop-2-enoate | 449172-19-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: [(3S,3'R,4'S,5'S,6'R)-6'-[[tert-butyl(dimethyl)silyl]oxymethyl]-4',5'-dihydroxy-4,6-bis[tri(propan-2-yl)silyloxy]spiro[1H-2-benzofuran-3,2'-oxane]-3'-yl] (E)-3-phenylprop-2-enoate
• CAS: 449172-19-4
• 化学式: C₄₆H₇₆O₉Si₃
• 分子量: 857.361
• InChiKey: HOKXRDZUVOJDKU-VLSBREPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.25
• 重原子数：
  58
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(3S,3'R,4'S,5'S,6'R)-6'-[[tert-butyl(dimethyl)silyl]oxymethyl]-4',5'-dihydroxy-4,6-bis[tri(propan-2-yl)silyloxy]spiro[1H-2-benzofuran-3,2'-oxane]-3'-yl] (E)-3-phenylprop-2-enoate 在 (trimethylsilyl)difluoride 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到[(3S,3'R,4'S,5'S,6'R)-4,4',5',6-tetrahydroxy-6'-(hydroxymethyl)spiro[1H-2-benzofuran-3,2'-oxane]-3'-yl] (E)-3-phenylprop-2-enoate
  参考文献：
  名称：

  A novel approach to the regioselective acylation of spirocyclic C-glucoside of papulacandins

  摘要：

  A novel approach to the regioselective acylation of spirocyclic C-glucosicle of papulacandins is reported. Conditions were found to effect regioselective acylation of triol 2 to give 2-O-acyl derivatives (5). which after deprotection with TASF afforded exclusively 2-O-acyl derivatives (8). An extensive migration of the acyl group from 2-O- to 3-O-position was observed when the desilylation was conducted with TBAF. These findings provided with a convenient means for extending the SAR of papulacandins at these position. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00664-0
• 作为产物：
  描述：

  肉桂酸 在 草酰氯 、 4 A molecular sieve 、 二正丁基氧化锡 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 21.0h， 生成 [(3S,3'R,4'S,5'S,6'R)-6'-[[tert-butyl(dimethyl)silyl]oxymethyl]-4',5'-dihydroxy-4,6-bis[tri(propan-2-yl)silyloxy]spiro[1H-2-benzofuran-3,2'-oxane]-3'-yl] (E)-3-phenylprop-2-enoate
  参考文献：
  名称：

  A novel approach to the regioselective acylation of spirocyclic C-glucoside of papulacandins

  摘要：

  A novel approach to the regioselective acylation of spirocyclic C-glucosicle of papulacandins is reported. Conditions were found to effect regioselective acylation of triol 2 to give 2-O-acyl derivatives (5). which after deprotection with TASF afforded exclusively 2-O-acyl derivatives (8). An extensive migration of the acyl group from 2-O- to 3-O-position was observed when the desilylation was conducted with TBAF. These findings provided with a convenient means for extending the SAR of papulacandins at these position. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00664-0

文献信息

• A novel approach to the regioselective acylation of spirocyclic C-glucoside of papulacandins
  作者：Chafiq Hamdouchi、Carlos Jaramillo、Javier Lopez-Prados、Almudena Rubio

  DOI：10.1016/s0040-4039(02)00664-0

  日期：2002.5

  A novel approach to the regioselective acylation of spirocyclic C-glucosicle of papulacandins is reported. Conditions were found to effect regioselective acylation of triol 2 to give 2-O-acyl derivatives (5). which after deprotection with TASF afforded exclusively 2-O-acyl derivatives (8). An extensive migration of the acyl group from 2-O- to 3-O-position was observed when the desilylation was conducted with TBAF. These findings provided with a convenient means for extending the SAR of papulacandins at these position. (C) 2002 Elsevier Science Ltd. All rights reserved.