(2R,3S,6R)-3-Methyl-6-[(S)-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-3,6-dihydro-2H-pyran-2-carboxylic acid | 153868-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2R,3S,6R)-3-Methyl-6-[(S)-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-3,6-dihydro-2H-pyran-2-carboxylic acid
• 英文别名: (2R,3S,6R)-3-methyl-6-[(2S)-1-(2-trimethylsilylethoxymethoxy)propan-2-yl]-3,6-dihydro-2H-pyran-2-carboxylic acid
• CAS: 153868-53-2
• 化学式: C₁₆H₃₀O₅Si
• 分子量: 330.497
• InChiKey: OMQDWPURKBEWPY-BYNSBNAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,6R)-3-Methyl-6-[(S)-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-3,6-dihydro-2H-pyran-2-carboxylic acid 在 palladium dihydroxide 、 四(三苯基膦)钯 咪唑 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 lithium tetrafluoroborate 、 正丁基锂 、 jones reagent 、 barium permanganate 、 四丁基氟化铵 、 氢气 、 sodium hexamethyldisilazane 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 115.84h， 生成 茚达霉素
  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：

  (5S,6R)-5-<(1S)-1-Methyl-2-<<2-(trimethylsilyl)ethoxy>methoxy>ethyl>-6-<(1E)-propenyl>-1,4-dioxan-2-one 在 三甲基氯硅烷 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 生成 (2R,3S,6R)-3-Methyl-6-[(S)-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-3,6-dihydro-2H-pyran-2-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.