[(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] (2E,4E)-5-(2-bromophenyl)penta-2,4-dienoate | 449172-21-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 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] (2E,4E)-5-(2-bromophenyl)penta-2,4-dienoate
• CAS: 449172-21-8
• 化学式: C₄₈H₇₇BrO₉Si₃
• 分子量: 962.294
• InChiKey: XBODYRBJTCGTSM-HYODDYBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.56
• 重原子数：
  61
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 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] (2E,4E)-5-(2-bromophenyl)penta-2,4-dienoate 在 (trimethylsilyl)difluoride 作用下， 以 四氢呋喃 为溶剂， 以85%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] (2E,4E)-5-(2-bromophenyl)penta-2,4-dienoate
  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：

  1,1,-anhydro-1-C-<6-(hydroxymethyl)-2,4-bis<(triisopropylsilyl)oxy>phenyl>-β-D-glucopyranose 在 咪唑 、 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 20.0h， 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] (2E,4E)-5-(2-bromophenyl)penta-2,4-dienoate
  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.