(1R,2S,5S)-2-<2-(tert-Butyloxy)-2-oxoethyl>-5-ethylcyclopentane-1-carboxylic acid | 153868-75-8

• 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: (1R,2S,5S)-2-<2-(tert-Butyloxy)-2-oxoethyl>-5-ethylcyclopentane-1-carboxylic acid
• 英文别名: (1R,2S,5S)-2-ethyl-5-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]cyclopentane-1-carboxylic acid
• CAS: 153868-75-8
• 化学式: C₁₄H₂₄O₄
• 分子量: 256.342
• InChiKey: LYAOOIOHPQOOKU-JBLDHEPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S,5S)-2-<2-(tert-Butyloxy)-2-oxoethyl>-5-ethylcyclopentane-1-carboxylic acid 在 trans-benzyl(chloro)-bis(triphenylphosphine)palladium(II) 、 N,N-二甲基甲酰胺 sodium tetrahydroborate 、 cerium(III) chloride 、 草酰氯 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 10.17h， 生成 tert-Butyl <(1S,2R,2(1R and 1S),3S)-3-ethyl-2-<(E)-1-hydroxy-5-(trimethylsilyl)-2-penten-4-ynyl>cyclopent-1-yl>acetate
  参考文献：
  名称：

  Total synthesis of ionophore antibiotic X-14547 A (indanomycin)

  摘要：

  A convergent, enantioselective total synthesis of ionophore antibiotic X-14547A (indanomycin, 1) is described. The dioxanone-to-dihydropyran variant of the lactonic Ireland-Claisen rearrangement establishes the hydropyran nucleus of the ''left wing'' fragment 2. Elaboration to the target synthon utilizes a new methodology for the preparation of stereodefined vinylsilanes (24 --> 25 --> 26) via net S(N)2' coupling of [alpha-(mesyloxy)allyl]silanes with Grignard reagents catalyzed by CuCN. Salient features in the construction of the ''right wing'' subunit 3 include a modification of the Noyori three-component coupling procedure (32 --> 33) and the application,of a retro hetero Diels-Alder/intramolecular Diels-Alder (''mock Claisen'') process (5 --> 39), Palladium-mediated cross Coupling of ''left wing'' and ''right wing'' synthons using Stille's method tolerates a free carboxylic acid and an unprotected acyl pyrrole, affording indanomycin directly in its natural absolute configuration.

  DOI：

  10.1021/jo00081a010
• 作为产物：
  描述：

  tert-Butyl <(1S,5R)-2-oxo-5-phenylcyclopent-3-en-1-yl>acetate 在 platinum(IV) oxide ruthenium trichloride 、 sodium periodate 、 CuI*P(n-Bu)3 、 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 28.0h， 生成 (1R,2S,5S)-2-<2-(tert-Butyloxy)-2-oxoethyl>-5-ethylcyclopentane-1-carboxylic acid
  参考文献：
  名称：

  Total synthesis of ionophore antibiotic X-14547 A (indanomycin)

  摘要：

  A convergent, enantioselective total synthesis of ionophore antibiotic X-14547A (indanomycin, 1) is described. The dioxanone-to-dihydropyran variant of the lactonic Ireland-Claisen rearrangement establishes the hydropyran nucleus of the ''left wing'' fragment 2. Elaboration to the target synthon utilizes a new methodology for the preparation of stereodefined vinylsilanes (24 --> 25 --> 26) via net S(N)2' coupling of [alpha-(mesyloxy)allyl]silanes with Grignard reagents catalyzed by CuCN. Salient features in the construction of the ''right wing'' subunit 3 include a modification of the Noyori three-component coupling procedure (32 --> 33) and the application,of a retro hetero Diels-Alder/intramolecular Diels-Alder (''mock Claisen'') process (5 --> 39), Palladium-mediated cross Coupling of ''left wing'' and ''right wing'' synthons using Stille's method tolerates a free carboxylic acid and an unprotected acyl pyrrole, affording indanomycin directly in its natural absolute configuration.

  DOI：

  10.1021/jo00081a010

文献信息

• Total synthesis of ionophore antibiotic X-14547 A (indanomycin)
  作者：Steven D. Burke、Anthony D. Piscopio、Michael E. Kort、Mark A. Matulenko、Marshall H. Parker、David M. Armistead、K. Shankaran

  DOI：10.1021/jo00081a010

  日期：1994.1

  A convergent, enantioselective total synthesis of ionophore antibiotic X-14547A (indanomycin, 1) is described. The dioxanone-to-dihydropyran variant of the lactonic Ireland-Claisen rearrangement establishes the hydropyran nucleus of the ''left wing'' fragment 2. Elaboration to the target synthon utilizes a new methodology for the preparation of stereodefined vinylsilanes (24 --> 25 --> 26) via net S(N)2' coupling of [alpha-(mesyloxy)allyl]silanes with Grignard reagents catalyzed by CuCN. Salient features in the construction of the ''right wing'' subunit 3 include a modification of the Noyori three-component coupling procedure (32 --> 33) and the application,of a retro hetero Diels-Alder/intramolecular Diels-Alder (''mock Claisen'') process (5 --> 39), Palladium-mediated cross Coupling of ''left wing'' and ''right wing'' synthons using Stille's method tolerates a free carboxylic acid and an unprotected acyl pyrrole, affording indanomycin directly in its natural absolute configuration.