(2R,3R,4S,5R,6S)-2-Allyloxy-3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-methyl-tetrahydro-pyran-4-ol | 239803-01-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6S)-2-Allyloxy-3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-methyl-tetrahydro-pyran-4-ol
• CAS: 239803-01-1
• 化学式: C₃₂H₄₀O₅Si
• 分子量: 532.752
• InChiKey: URKALXFUFFREFK-WAOXQYERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  38.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 (2R,3R,4S,5R,6S)-2-Allyloxy-3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-methyl-tetrahydro-pyran-4-ol 在 2,6-二甲基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以100%的产率得到1-O-allyl-2-O-benzyl-3-O-(tert-butyldimethylsilyl)-4-O-(tert-butyldiphenylsilyl)-α-L-rhamnopyranoside
  参考文献：
  名称：

  Stable axial-rich conformation of pyranoses derived from L-rhamnose and D-mannose

  摘要：

  Stable chair conformation with more axial substituents (axial-rich conformation) of pyranoses derived from L-rhamnose and D-mannose is described. The naturally stable ring conformation of L-rhamnose (C-1(4)) and D-mannose (C-4(1)) was flipped by introduction of a TBS group into a hydroxyl group at C-3 and a TPS group into a hydroxyl group at C-4 to give C-4(1) and C-1(4) conformers, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01077-1
• 作为产物：
  描述：

  allyl 2,3-O-benzylidene-α-L-rhamnoside 在 咪唑 、 4-二甲氨基吡啶 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 44.0h， 生成 (2R,3R,4S,5R,6S)-2-Allyloxy-3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-methyl-tetrahydro-pyran-4-ol
  参考文献：
  名称：

  Stable axial-rich conformation of pyranoses derived from L-rhamnose and D-mannose

  摘要：

  Stable chair conformation with more axial substituents (axial-rich conformation) of pyranoses derived from L-rhamnose and D-mannose is described. The naturally stable ring conformation of L-rhamnose (C-1(4)) and D-mannose (C-4(1)) was flipped by introduction of a TBS group into a hydroxyl group at C-3 and a TPS group into a hydroxyl group at C-4 to give C-4(1) and C-1(4) conformers, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01077-1