(4R,5R,8S,E)-ethyl 9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-2-enoate | 1123785-30-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4R,5R,8S,E)-ethyl 9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-2-enoate
• 英文别名: ethyl (E,4R,5R,8S)-5-[tert-butyl(dimethyl)silyl]oxy-4,8-dimethyl-9-phenylmethoxynon-2-enoate
• CAS: 1123785-30-7
• 化学式: C₂₆H₄₄O₄Si
• 分子量: 448.718
• InChiKey: XPKFDQUYVQJYMO-BQUITJOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.77
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5R,8S,E)-ethyl 9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-2-enoate 在 sodium chlorite 、 sodium dihydrogenphosphate 、 lithium aluminium tetrahydride 、 2-甲基-2-丁烯 、 2,2,6,6-四甲基哌啶氧化物 、 zinc(II) nitrate hexahydrate 、 nickel(II) chloride hexahydrate 、 hexaammonium heptamolybdate tetrahydrate 、 碘苯二乙酸 、 偶氮二甲酸二异丙酯 、 氨 、 双氧水 、 lithium 、 双(三甲基硅烷基)氨基钾 、 sodium hydride 、 二正丁基氧化锡 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 氘代四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 水 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 反应 24.0h， 生成 (2S,5R,6R,11S,9E)-12-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-11-hydroxy-2,6-dimethyldodec-9-enoic acid
  参考文献：
  名称：

  Asymmetric synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W from 4-pentenoic acid

  摘要：

  A flexible and efficient asymmetric route to the synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W has been accomplished from commercially available 4-pentenoic acid. The successful generation of stereocenters was achieved by utilizing an Evans' chiral auxiliary-based alkylation and aldol reaction. Other key reactions such as a Julia-Kocienski olefination, Kita's macrolactonization, ring closing metathesis (RCM) reaction, and Yamaguchi's esterification were significant for the construction of the macrolactone cores. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.006
• 作为产物：
  描述：

  (S)-(-)-2-methyl-4-penten-1-ol 在 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 重铬酸吡啶 、 dimethyl sulfide borane 、 三氟甲磺酸二丁硼 、 sodium hydride 、 戴斯-马丁氧化剂 、 乙氧甲酰基亚甲基三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 56.67h， 生成 (4R,5R,8S,E)-ethyl 9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-2-enoate
  参考文献：
  名称：

  Asymmetric synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W from 4-pentenoic acid

  摘要：

  A flexible and efficient asymmetric route to the synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W has been accomplished from commercially available 4-pentenoic acid. The successful generation of stereocenters was achieved by utilizing an Evans' chiral auxiliary-based alkylation and aldol reaction. Other key reactions such as a Julia-Kocienski olefination, Kita's macrolactonization, ring closing metathesis (RCM) reaction, and Yamaguchi's esterification were significant for the construction of the macrolactone cores. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.006

文献信息

• Highly stereoselective approach toward the synthesis of the macrolactone core of amphidinolide W
  作者：Debendra K. Mohapatra、Bhaskar Chatterjee、Mukund K. Gurjar

  DOI：10.1016/j.tetlet.2008.11.088

  日期：2009.2

  The diastereoselective synthesis of the macrolactone core of amphidinolide W was successfully accomplished using Evans’ asymmetric alkylation, Aldol reaction, Julia-Kocienski olefination, and Kita’s macrocyclization protocol.

  使用Evans的不对称烷基化，Aldol反应，Julia-Kocienski烯烃化反应和Kita的大环化方案成功完成了安非他命W的大内酯核的非对映选择性合成。
• Asymmetric synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W from 4-pentenoic acid
  作者：Bhaskar Chatterjee、Dhananjoy Mondal、Smritilekha Bera

  DOI：10.1016/j.tetasy.2012.07.006

  日期：2012.8

  A flexible and efficient asymmetric route to the synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W has been accomplished from commercially available 4-pentenoic acid. The successful generation of stereocenters was achieved by utilizing an Evans' chiral auxiliary-based alkylation and aldol reaction. Other key reactions such as a Julia-Kocienski olefination, Kita's macrolactonization, ring closing metathesis (RCM) reaction, and Yamaguchi's esterification were significant for the construction of the macrolactone cores. (c) 2012 Elsevier Ltd. All rights reserved.