7-allyl-8-benzyloxy-6-isopropoxy-2-phenyl-4a-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol | 918302-27-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 7-allyl-8-benzyloxy-6-isopropoxy-2-phenyl-4a-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol
• CAS: 918302-27-9
• 化学式: C₂₈H₃₄O₆
• 分子量: 466.574
• InChiKey: ZXPLKJJXLSMFJH-UBUZFBQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  7-allyl-8-benzyloxy-6-isopropoxy-2-phenyl-4a-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到
  参考文献：
  名称：

  RCM as a tool to freeze conformation of monosaccharides: synthesis of a β-mannopyranoside mimic adopting a conformation close to the biologically relevant B2,5 boat

  摘要：

  The synthesis of a P-D-mannopyranoside analog, fully identical to the naturally occurring D-mannopyranose in terms of hydroxyl pattern, and displaying a skew-boat conformation close to a B-2,B-5 boat strongly believed to be adopted by the oxycarbenium transition state during glycosidic bond cleavage of beta-mannane by family 26 beta-mannanase, is described. The conformationally locked analog has been obtained by tethering the C-2 and C-5 carbon atoms of the sugar ring with a three carbon bridge using RCM methodology. Conformation of the mannose analog has been confirmed by NMR and molecular modelling. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.046
• 作为产物：
  描述：

  (2R,3S,4S,5R,6R)-4-Benzyloxy-2-hydroxymethyl-6-isopropoxy-2-vinyl-tetrahydro-pyran-3,5-diol 在 草酰氯 、 camphor-10-sulfonic acid 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 7-allyl-8-benzyloxy-6-isopropoxy-2-phenyl-4a-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol
  参考文献：
  名称：

  RCM as a tool to freeze conformation of monosaccharides: synthesis of a β-mannopyranoside mimic adopting a conformation close to the biologically relevant B2,5 boat

  摘要：

  The synthesis of a P-D-mannopyranoside analog, fully identical to the naturally occurring D-mannopyranose in terms of hydroxyl pattern, and displaying a skew-boat conformation close to a B-2,B-5 boat strongly believed to be adopted by the oxycarbenium transition state during glycosidic bond cleavage of beta-mannane by family 26 beta-mannanase, is described. The conformationally locked analog has been obtained by tethering the C-2 and C-5 carbon atoms of the sugar ring with a three carbon bridge using RCM methodology. Conformation of the mannose analog has been confirmed by NMR and molecular modelling. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.046