isobutyric acid 2-allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isobutyric acid 2-allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester
• 英文别名: [(2S,3S,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-prop-2-enyloxan-3-yl] 2-methylpropanoate
• 化学式: C₃₄H₄₀O₆
• 分子量: 544.688
• InChiKey: CXOGHVLLVDCRLC-MPJBSJSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  isobutyric acid 2-allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 、 二溴甲烷 在 lead(II) chloride 四甲基乙二胺 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 以62%的产率得到3,4-dibenzyloxy-2-benzyloxymethyl-6-isopropyl-2,3,4,4a,8,8a-hexahydro-pyrano[3,2-b]pyran
  参考文献：
  名称：

  Olefinic-ester cyclizations using Takai–Utimoto reduced titanium alkylidenes

  摘要：

  The scope and limitations of the Takai-Utimoto reagent to induce the cyclization of olefinic-esters is described. Critical is the steric environment about both the ester and the olefin. Mechanistically, these results support the hypothesis that cyclized product comes from an olefin metathesis, carbonyl-olefination sequence. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.071

文献信息

• Olefinic-ester cyclizations using Takai–Utimoto reduced titanium alkylidenes
  作者：Utpal Majumder、Jon D. Rainier

  DOI：10.1016/j.tetlet.2005.08.071

  日期：2005.10

  The scope and limitations of the Takai-Utimoto reagent to induce the cyclization of olefinic-esters is described. Critical is the steric environment about both the ester and the olefin. Mechanistically, these results support the hypothesis that cyclized product comes from an olefin metathesis, carbonyl-olefination sequence. (c) 2005 Elsevier Ltd. All rights reserved.