(8Z,12E)-(2S,3R,4S,11S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-1-{1-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-cyclopropyl}-2,4,8,12-tetramethyl-13-(2-methyl-thiazol-4-yl)-trideca-8,12-dien-1-one | 203252-91-9

• 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
• 英文名称: (8Z,12E)-(2S,3R,4S,11S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-1-{1-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-cyclopropyl}-2,4,8,12-tetramethyl-13-(2-methyl-thiazol-4-yl)-trideca-8,12-dien-1-one
• CAS: 203252-91-9
• 化学式: C₄₅H₈₅NO₅SSi₃
• 分子量: 836.496
• InChiKey: CDBKZQLZEYCLTM-PFHURZKCSA-N

反应信息

• 作为反应物：
  描述：

  (8Z,12E)-(2S,3R,4S,11S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-1-{1-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-cyclopropyl}-2,4,8,12-tetramethyl-13-(2-methyl-thiazol-4-yl)-trideca-8,12-dien-1-one 在 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 、 四丁基氟化铵 、 氟化氢吡啶 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 37.5h， 生成 (Z)-(4S,8S,15S,16R,17S)-4,16-Dihydroxy-11,15,17-trimethyl-8-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-7-oxa-spiro[2.15]octadec-10-ene-6,18-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：

  (8Z,12E)-(2S,3R,4S,11S)-1-{1-[(S)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-cyclopropyl}-3,11-bis-(tert-butyl-dimethyl-silanyloxy)-2,4,8,12-tetramethyl-13-(2-methyl-thiazol-4-yl)-trideca-8,12-dien-1-one 在 camphor-10-sulfonic acid 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以60%的产率得到(8Z,12E)-(2S,3R,4S,11S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-1-{1-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-cyclopropyl}-2,4,8,12-tetramethyl-13-(2-methyl-thiazol-4-yl)-trideca-8,12-dien-1-one
  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