methyl 3-[(2S,3S)-3-[(2S,5S,7S)-7-[(2S)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-1,6-dioxaspiro[4.5]decan-2-yl]-2-methyloxiran-2-yl]-2-triethylsilyloxypropanoate | 931113-67-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3-[(2S,3S)-3-[(2S,5S,7S)-7-[(2S)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-1,6-dioxaspiro[4.5]decan-2-yl]-2-methyloxiran-2-yl]-2-triethylsilyloxypropanoate
• CAS: 931113-67-6
• 化学式: C₄₀H₆₂O₇Si₂
• 分子量: 711.099
• InChiKey: PSEAADZAKGNIQR-OUYSFJCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.75
• 重原子数：
  49
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  75.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-[(2S,3S)-3-[(2S,5S,7S)-7-[(2S)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-1,6-dioxaspiro[4.5]decan-2-yl]-2-methyloxiran-2-yl]-2-triethylsilyloxypropanoate 在 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 [(2S)-2-[(2S,5S,7S)-2-[(2S,3S)-3-[(Z,6S,9R)-6,9-bis[(4-methoxyphenyl)methoxy]-6-methyl-9-[(2R,5R)-5-methyl-5-(phenylmethoxymethyl)oxolan-2-yl]-2-triethylsilyloxynon-3-enyl]-3-methyloxiran-2-yl]-1,6-dioxaspiro[4.5]decan-7-yl]propoxy]-tert-butyl-diphenylsilane
  参考文献：
  名称：

  Pectenotoxin-2 Synthetic Studies. 3. Assessment of the Capacity for Stereocontrolled Cyclization To Form the Entire C1−C26 Subunit Based upon the Double Bond Geometry Across C15-C16

  摘要：

  Second-generation synthetic routes to enantiopure sulfone 21 and aldehyde 24 are described. The union of these two intermediates by means of a Julia-Kocienski coupling gave rise to a series of E-configured building blocks that did not prove amenable to transannular cyclization. Alternatively, when the C15-C16 double bond was introduced with Z-geometry by Wittig olefination, spontaneous closure to generate a tetrahydrofuran culminated an ensuing direct dihydroxylation step. The structural assignment to 35, undergirded by detailed H-1 and C-13 NMR studies, is consistent with proper transannular bonding so as to deliver the entire C1-C26 fragment of PTX2.

  DOI：

  10.1021/jo062513f
• 作为产物：
  描述：

  3-((2S,3S)-3-{(2S,5S,7S)-7-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-1,6-dioxa-spiro[4.5]dec-2-yl}-2-methyl-oxiranyl)-2-hydroxy-propionic acid methyl ester 、 三乙基氯硅烷 在 4-二甲氨基吡啶 、 二异丙胺 作用下， 以100%的产率得到methyl 3-[(2S,3S)-3-[(2S,5S,7S)-7-[(2S)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-1,6-dioxaspiro[4.5]decan-2-yl]-2-methyloxiran-2-yl]-2-triethylsilyloxypropanoate
  参考文献：
  名称：

  Pectenotoxin-2 Synthetic Studies. 3. Assessment of the Capacity for Stereocontrolled Cyclization To Form the Entire C1−C26 Subunit Based upon the Double Bond Geometry Across C15-C16

  摘要：

  Second-generation synthetic routes to enantiopure sulfone 21 and aldehyde 24 are described. The union of these two intermediates by means of a Julia-Kocienski coupling gave rise to a series of E-configured building blocks that did not prove amenable to transannular cyclization. Alternatively, when the C15-C16 double bond was introduced with Z-geometry by Wittig olefination, spontaneous closure to generate a tetrahydrofuran culminated an ensuing direct dihydroxylation step. The structural assignment to 35, undergirded by detailed H-1 and C-13 NMR studies, is consistent with proper transannular bonding so as to deliver the entire C1-C26 fragment of PTX2.

  DOI：

  10.1021/jo062513f

文献信息

• Pectenotoxin-2 Synthetic Studies. 3. Assessment of the Capacity for Stereocontrolled Cyclization To Form the Entire C1−C26 Subunit Based upon the Double Bond Geometry Across C15-C16
  作者：Patrick D. O'Connor、Christopher K. Knight、Dirk Friedrich、Xiaowen Peng、Leo A. Paquette

  DOI：10.1021/jo062513f

  日期：2007.3.1

  Second-generation synthetic routes to enantiopure sulfone 21 and aldehyde 24 are described. The union of these two intermediates by means of a Julia-Kocienski coupling gave rise to a series of E-configured building blocks that did not prove amenable to transannular cyclization. Alternatively, when the C15-C16 double bond was introduced with Z-geometry by Wittig olefination, spontaneous closure to generate a tetrahydrofuran culminated an ensuing direct dihydroxylation step. The structural assignment to 35, undergirded by detailed H-1 and C-13 NMR studies, is consistent with proper transannular bonding so as to deliver the entire C1-C26 fragment of PTX2.