(E)-3-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-ethynyl-6-methoxy-tetrahydro-pyran-3-yloxy)-acrylic acid ethyl ester | 273926-05-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-3-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-ethynyl-6-methoxy-tetrahydro-pyran-3-yloxy)-acrylic acid ethyl ester
• 英文别名: ethyl (E)-3-[(2R,3R,4S,5R,6S)-2-ethynyl-6-methoxy-4,5-bis(phenylmethoxy)oxan-3-yl]oxyprop-2-enoate
• CAS: 273926-05-9
• 化学式: C₂₇H₃₀O₇
• 分子量: 466.531
• InChiKey: BIWJDQBDRKTAEF-UAMZORIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 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-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-ethynyl-6-methoxy-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 11.5h， 以85%的产率得到((2R,3aR,5S,6R,7S,7aR)-6,7-Bis-benzyloxy-5-methoxy-3-methylene-hexahydro-furo[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：

  methyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-α-D-glucopyranoside 在 N-甲基吗啉 、 戴斯-马丁氧化剂 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 (E)-3-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-ethynyl-6-methoxy-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.