(3S,3'R,4'S,5'S,6'R)-6'-[[tert-butyl(dimethyl)silyl]oxymethyl]-4,6-bis[tri(propan-2-yl)silyloxy]spiro[1H-2-benzofuran-3,2'-oxane]-3',4',5'-triol | 449172-15-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: (3S,3'R,4'S,5'S,6'R)-6'-[[tert-butyl(dimethyl)silyl]oxymethyl]-4,6-bis[tri(propan-2-yl)silyloxy]spiro[1H-2-benzofuran-3,2'-oxane]-3',4',5'-triol
• CAS: 449172-15-0
• 化学式: C₃₇H₇₀O₈Si₃
• 分子量: 727.214
• InChiKey: FKTLYOZSCLCTSY-WUDHZMGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.98
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  8

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]-4,6-bis[tri(propan-2-yl)silyloxy]spiro[1H-2-benzofuran-3,2'-oxane]-3',4',5'-triol 在 4 A molecular sieve 、 四丁基氟化铵 、 二正丁基氧化锡 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 20.0h， 生成 [(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：

  叔丁基二甲硅基三氟甲磺酸酯 、 1,1,-anhydro-1-C-<6-(hydroxymethyl)-2,4-bis<(triisopropylsilyl)oxy>phenyl>-β-D-glucopyranose 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以100%的产率得到(3S,3'R,4'S,5'S,6'R)-6'-[[tert-butyl(dimethyl)silyl]oxymethyl]-4,6-bis[tri(propan-2-yl)silyloxy]spiro[1H-2-benzofuran-3,2'-oxane]-3',4',5'-triol
  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.