methyl 2-[(1S,2S,6R,7S,9S,12R)-7-[(1S)-1,2-dihydroxyethyl]-4,4-dimethyl-3,5,8,13-tetraoxatricyclo[7.4.0.02,6]tridecan-12-yl]acetate | 153580-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: methyl 2-[(1S,2S,6R,7S,9S,12R)-7-[(1S)-1,2-dihydroxyethyl]-4,4-dimethyl-3,5,8,13-tetraoxatricyclo[7.4.0.02,6]tridecan-12-yl]acetate
• CAS: 153580-61-1
• 化学式: C₁₆H₂₆O₈
• 分子量: 346.378
• InChiKey: URWGYZGGYXTIMF-BCLBKFSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2-[(1S,2S,6R,7S,9S,12R)-7-[(1S)-1,2-dihydroxyethyl]-4,4-dimethyl-3,5,8,13-tetraoxatricyclo[7.4.0.02,6]tridecan-12-yl]acetate 生成
  参考文献：
  名称：

  Synthetic studies on halichondrins: A practical synthesis of the C.1C.13 segment

  摘要：

  A practical, scalable synthesis of the C.1-C.13 segment of halichondrin B has been developed starting from L-mannonic-gamma-lactone, using C-allylation/oxy-Michael cyclization and Ni(II)/Cr(II)-mediated vinyltrimethylsilane addition to set the C.6/C.3 and C.11 stereocenters, respectively. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)01999-5
• 作为产物：
  描述：

  (4R,5R)-5-[(S)-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 在 RhCl(PPh₃)3 吡啶 、 4-二甲氨基吡啶 、 pyridinium chlorochromate absorbed on neutral alumina 、 四氧化锇 、 N,N'-二异丙基乙二胺 、 三氟甲磺酸三甲基硅酯 、 potassium tert-butylate 、 对甲苯磺酸 、 三甲基苯甲氧基胺 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 methyl 2-[(1S,2S,6R,7S,9S,12R)-7-[(1S)-1,2-dihydroxyethyl]-4,4-dimethyl-3,5,8,13-tetraoxatricyclo[7.4.0.02,6]tridecan-12-yl]acetate
  参考文献：
  名称：

  Synthetic studies on halichondrins: A new practical synthesis of the C.1–C.12 segment

  摘要：

  A new practical synthesis of the C.1-C.12 halichondrin segment was achieved from L-mannonic gamma-lactone (5), using osmylation, C-allylation and Michael reaction as key steps.

  DOI：

  10.1016/s0040-4039(00)60394-5

文献信息

• Synthetic studies on halichondrins: A new practical synthesis of the C.1–C.12 segment
  作者：James J.-W. Duan、Yoshito Kishi

  DOI：10.1016/s0040-4039(00)60394-5

  日期：1993.11

  A new practical synthesis of the C.1-C.12 halichondrin segment was achieved from L-mannonic gamma-lactone (5), using osmylation, C-allylation and Michael reaction as key steps.
• Synthetic studies on halichondrins: A practical synthesis of the C.1C.13 segment
  作者：Dean P Stamos、Yoshito Kishi

  DOI：10.1016/s0040-4039(96)01999-5

  日期：1996.11

  A practical, scalable synthesis of the C.1-C.13 segment of halichondrin B has been developed starting from L-mannonic-gamma-lactone, using C-allylation/oxy-Michael cyclization and Ni(II)/Cr(II)-mediated vinyltrimethylsilane addition to set the C.6/C.3 and C.11 stereocenters, respectively. Copyright (C) 1996 Elsevier Science Ltd