| 209260-60-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• CAS: 209260-60-6
• 化学式: C₂₄H₄₁NO₃Si
• 分子量: 419.68
• InChiKey: BQXPAHGCMSFKQN-PTUTZOHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.12
• 重原子数：
  29.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.33
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 草酰氯 、 2,4,6-三氯苯甲酰氯 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 氟化氢吡啶 、 二甲基亚砜 、 三乙胺 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 氯仿 、 叔丁醇 为溶剂， 反应 55.0h， 生成 (1R,3S,7S,10R,11S,12S,16S)-7,11-Dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-methyl-2-(2-methyl-oxazol-4-yl)-vinyl]-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione
  参考文献：
  名称：

  Total Synthesis of Oxazole- and Cyclopropane-Containing Epothilone B Analogues by the Macrolactonization Approach

  摘要：

  AbstractIn order to probe structure‐activity relationships in the epothilone area, two series of epothilone B analogues have been designed and synthesized. The first series containing an oxazole moiety in place of a thiazole on the side chain was constructed by utilizing key intermediates 7–9 or 10, 12, and 13 (Scheme 1), whereas the second series containing an ethano group instead of the gem‐dimethyl group at position 4 was synthesized from fragments 42 and 43. A Yamaguchi‐type macrolactonization reaction was used to construct the macrocycle from a secoacid, which was assembled, in both cases, by means of a) an aldol reaction, b) an Enders alkylation, and c) a Wittig‐type reaction. This convergent strategy provided access to oxazole analogues 2,4,29–32 and 4,4‐ethano derivatives 3,40,60–63 for biological studies.

  DOI：

  10.1002/chem.19970031212
• 作为产物：
  描述：

  (E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-5-(2-methyl-oxazol-4-yl)-pent-4-enal 在 咪唑 、 sodium tetrahydroborate 、 pyridine-SO3 complex 、 camphor-10-sulfonic acid 、 碘 、 sodium hexamethyldisilazane 、 二甲基亚砜 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 19.0h， 生成
  参考文献：
  名称：

  Total Synthesis of Oxazole- and Cyclopropane-Containing Epothilone B Analogues by the Macrolactonization Approach

  摘要：

  AbstractIn order to probe structure‐activity relationships in the epothilone area, two series of epothilone B analogues have been designed and synthesized. The first series containing an oxazole moiety in place of a thiazole on the side chain was constructed by utilizing key intermediates 7–9 or 10, 12, and 13 (Scheme 1), whereas the second series containing an ethano group instead of the gem‐dimethyl group at position 4 was synthesized from fragments 42 and 43. A Yamaguchi‐type macrolactonization reaction was used to construct the macrocycle from a secoacid, which was assembled, in both cases, by means of a) an aldol reaction, b) an Enders alkylation, and c) a Wittig‐type reaction. This convergent strategy provided access to oxazole analogues 2,4,29–32 and 4,4‐ethano derivatives 3,40,60–63 for biological studies.

  DOI：

  10.1002/chem.19970031212