(E)-3-((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-acrylic acid ethyl ester | 273926-00-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-3-((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-acrylic acid ethyl ester
• 英文别名: ethyl (E)-3-[(2S,3S,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-prop-2-ynyloxan-3-yl]oxyprop-2-enoate
• CAS: 273926-00-4
• 化学式: C₃₅H₃₈O₇
• 分子量: 570.683
• InChiKey: XMKHVECNXVCTQR-ZZNVUCROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-3-((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-acrylic acid ethyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 、 对甲苯磺酸 作用下， 以 甲苯 、 二氯甲烷 为溶剂， 反应 13.5h， 以71%的产率得到((2S,4aS,6R,7R,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-3-methylene-octahydro-pyrano[3,2-b]pyran-2-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  Radical Cyclization of Sugar-Derived β-(Alkynyloxy)acrylates:  Synthesis of Novel Fused Ethers

  摘要：

  Tributyltin radical mediated cyclization of carbohydrate-derived beta-(alkynyloxy)acrylates leading to highly functionalized cis and trans-fused bicyclic ethers of various ring sizes is described. The efficacy of the radical cyclization is nicely illustrated in the iterative construction of a trans-fused tricyclic tetrahydropyran.

  DOI：

  10.1021/ol0000408
• 作为产物：
  描述：

  3,4,6-tri-O-benzyl-D-glucal epoxide 在 N-甲基吗啉 、 正丁基锂 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-3-((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-acrylic acid ethyl ester
  参考文献：
  名称：

  Radical Cyclization of Sugar-Derived β-(Alkynyloxy)acrylates:  Synthesis of Novel Fused Ethers

  摘要：

  Tributyltin radical mediated cyclization of carbohydrate-derived beta-(alkynyloxy)acrylates leading to highly functionalized cis and trans-fused bicyclic ethers of various ring sizes is described. The efficacy of the radical cyclization is nicely illustrated in the iterative construction of a trans-fused tricyclic tetrahydropyran.

  DOI：

  10.1021/ol0000408

文献信息

• Radical Cyclization of Sugar-Derived β-(Alkynyloxy)acrylates:  Synthesis of Novel Fused Ethers
  作者：Michiel A. Leeuwenburgh、Remy E. J. N. Litjens、Jeroen D. C. Codée、Herman S. Overkleeft、Gijsbert A. van der Marel、Jacques H. van Boom

  DOI：10.1021/ol0000408

  日期：2000.5.1

  Tributyltin radical mediated cyclization of carbohydrate-derived beta-(alkynyloxy)acrylates leading to highly functionalized cis and trans-fused bicyclic ethers of various ring sizes is described. The efficacy of the radical cyclization is nicely illustrated in the iterative construction of a trans-fused tricyclic tetrahydropyran.