(3S,6R)-3,6-bis(4-methoxybenzyloxy)-6-((2R,5R)-5-(benzyloxymethyl)-5-methyl-tetrahydrofuran-2-yl)-3-methylhexan-1-ol | 931113-64-3

• 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: (3S,6R)-3,6-bis(4-methoxybenzyloxy)-6-((2R,5R)-5-(benzyloxymethyl)-5-methyl-tetrahydrofuran-2-yl)-3-methylhexan-1-ol
• 英文别名: (3S,6R)-3,6-bis[(4-methoxyphenyl)methoxy]-3-methyl-6-[(2R,5R)-5-methyl-5-(phenylmethoxymethyl)oxolan-2-yl]hexan-1-ol
• CAS: 931113-64-3
• 化学式: C₃₆H₄₈O₇
• 分子量: 592.773
• InChiKey: GOISICOJINDVQQ-PEDCNLCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  43
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3S,6R)-3,6-bis(4-methoxybenzyloxy)-6-((2R,5R)-5-(benzyloxymethyl)-5-methyl-tetrahydrofuran-2-yl)-3-methylhexan-1-ol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 苯 为溶剂， 反应 1.0h， 以67%的产率得到(2R,5R)-5-[(1R,4S)-6-iodo-1,4-bis[(4-methoxyphenyl)methoxy]-4-methylhexyl]-2-methyl-2-(phenylmethoxymethyl)oxolane
  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：

  tert-butyldimethyl((4-methylpent-4-en-1-yl)oxy)silane 在 potassium osmate(VI) 、 dipotassium peroxodisulfate 、 potassium dioxotetrahydroxoosmate(VI) 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 Hydroquinone 1,4-phthalazinediyl diether 、 偶氮二甲酸二异丙酯 、 mercury(II) diacetate 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 potassium hydride 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 potassium carbonate 、 戴斯-马丁氧化剂 、 甲基磺酰氯 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 三乙胺 、 间氯过氧苯甲酸 、 三苯基膦 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 163.41h， 生成 (3S,6R)-3,6-bis(4-methoxybenzyloxy)-6-((2R,5R)-5-(benzyloxymethyl)-5-methyl-tetrahydrofuran-2-yl)-3-methylhexan-1-ol
  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.