(Z)-(S)-4-Hydroxy-pent-2-enoic acid ((2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,4R,5R,7S)-4-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-7-methyl-1,6-dioxa-spiro[2.5]oct-5-yl]-3-methyl-penta-2,4-dienyl}-2,5-dimethyl-tetrahydro-pyran-3-yl)-amide | 878673-41-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-(S)-4-Hydroxy-pent-2-enoic acid ((2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,4R,5R,7S)-4-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-7-methyl-1,6-dioxa-spiro[2.5]oct-5-yl]-3-methyl-penta-2,4-dienyl}-2,5-dimethyl-tetrahydro-pyran-3-yl)-amide
• 英文别名: (Z,4S)-N-[(2R,3R,5S,6S)-6-[(2E,4E)-5-[(3R,4R,5R,7S)-4-[tert-butyl(dimethyl)silyl]oxy-7-methoxy-7-methyl-1,6-dioxaspiro[2.5]octan-5-yl]-3-methylpenta-2,4-dienyl]-2,5-dimethyloxan-3-yl]-4-hydroxypent-2-enamide
• CAS: 878673-41-7
• 化学式: C₃₂H₅₅NO₇Si
• 分子量: 593.877
• InChiKey: VYRZWXVMRDJJSC-LDTJKNCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (Z)-(S)-4-Hydroxy-pent-2-enoic acid ((2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,4R,5R,7S)-4-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-7-methyl-1,6-dioxa-spiro[2.5]oct-5-yl]-3-methyl-penta-2,4-dienyl}-2,5-dimethyl-tetrahydro-pyran-3-yl)-amide 在 4-二甲氨基吡啶 、 Amberlyst 15 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 24.5h， 生成 4(S)-乙酰氧基-N-[(2R,3R,5S,6S)-6-[5-[(3R,4R,5R,7S)-4,7-二羟基-7-甲基-1,6-二氧杂螺[2.5]辛烷-5-基]-3-甲基-2(E),4(E)-戊二烯基]-2,5-二甲基四氢吡喃-3-基]-2(Z)-戊烯酰胺
  参考文献：
  名称：

  Total synthesis of FR901464: second generation

  摘要：

  FR901464, a potent cell cycle inhibitor, was synthesized in a convergent manner using natural chiral Pool, L-threonine, ethyl (S)-lactate and 2-deoxy-D-glucose as starting materials. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2005.11.031
• 作为产物：
  描述：

  (S,Z)-methyl 4-((tert-butyldimethylsilyl)oxy)pent-2-enoate 在 N-乙基吗啉 、 盐酸 、 lithium hydroxide 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 、 乙腈 为溶剂， 反应 31.0h， 生成 (Z)-(S)-4-Hydroxy-pent-2-enoic acid ((2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,4R,5R,7S)-4-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-7-methyl-1,6-dioxa-spiro[2.5]oct-5-yl]-3-methyl-penta-2,4-dienyl}-2,5-dimethyl-tetrahydro-pyran-3-yl)-amide
  参考文献：
  名称：

  Total synthesis of FR901464: second generation

  摘要：

  FR901464, a potent cell cycle inhibitor, was synthesized in a convergent manner using natural chiral Pool, L-threonine, ethyl (S)-lactate and 2-deoxy-D-glucose as starting materials. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2005.11.031

文献信息

• Total synthesis of FR901464: second generation
  作者：Hajime Motoyoshi、Masato Horigome、Hidenori Watanabe、Takeshi Kitahara

  DOI：10.1016/j.tet.2005.11.031

  日期：2006.2

  FR901464, a potent cell cycle inhibitor, was synthesized in a convergent manner using natural chiral Pool, L-threonine, ethyl (S)-lactate and 2-deoxy-D-glucose as starting materials. (c) 2005 Published by Elsevier Ltd.