(2R,3R,4S,5S,6R)-2-[(1S,2R)-3-hydroxy-1-bromo-2-methylpropyl]-6-[(1,1-dimethyl)ethyldimethylsilyloxymethyl]-3-methanesulfonyl-2,4,6-trimethyl-5-trimethylsilyloxytetrahydropyran | 286458-78-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5S,6R)-2-[(1S,2R)-3-hydroxy-1-bromo-2-methylpropyl]-6-[(1,1-dimethyl)ethyldimethylsilyloxymethyl]-3-methanesulfonyl-2,4,6-trimethyl-5-trimethylsilyloxytetrahydropyran
• 英文别名: [(2R,3R,4S,5S,6R)-2-[(1S,2R)-1-bromo-3-hydroxy-2-methylpropyl]-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,4,6-trimethyl-5-trimethylsilyloxyoxan-3-yl] methanesulfonate
• CAS: 286458-78-4
• 化学式: C₂₃H₄₉BrO₇SSi₂
• 分子量: 605.779
• InChiKey: GJLGGKCQELTABI-XPOUZDIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2R,3R,4S,5S,6R)-2-[(1S,2R)-3-hydroxy-1-bromo-2-methylpropyl]-6-[(1,1-dimethyl)ethyldimethylsilyloxymethyl]-3-methanesulfonyl-2,4,6-trimethyl-5-trimethylsilyloxytetrahydropyran 以 吡啶 为溶剂， 反应 1.0h， 以85%的产率得到(2R,3R,4S,5S,6R)-2-[(1S,2R)-3-acetyloxy-1-bromo-2-methylpropyl]-6-[(1,1-dimethyl)ethyldimethylsilyloxymethyl]-3-methanesulfonyl-2,4,6-trimethyl-5-trimethylsilyloxytetrahydropyran
  参考文献：
  名称：

  Efficient Synthesis of the C₁−C₁₁ Fragment of the Tedanolides. The Nonaldol Aldol Process in Synthesis

  摘要：

  [GRAPHICS]The nonaldol aldol process developed in our laboratories has been applied to the synthesis of a C-1-C-11 fragment 22 of the novel macrocyclic cytotoxic agents tedanolide and 13-deoxytedanolide 1 and 2. The commercially available hydroxy ester 7 was converted in 24 steps into compound 22 using two nonaldol aldol reactions.

  DOI：

  10.1021/ol005675l
• 作为产物：
  描述：

  (2R,3S,4R)-3-Bromo-2,4-dimethyl-tetrahydro-furan-2-carbaldehyde 在 咪唑 、 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 、 四丁基氟化铵 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 、 癸烷 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 19.83h， 生成 (2R,3R,4S,5S,6R)-2-[(1S,2R)-3-hydroxy-1-bromo-2-methylpropyl]-6-[(1,1-dimethyl)ethyldimethylsilyloxymethyl]-3-methanesulfonyl-2,4,6-trimethyl-5-trimethylsilyloxytetrahydropyran
  参考文献：
  名称：

  Efficient Synthesis of the C₁−C₁₁ Fragment of the Tedanolides. The Nonaldol Aldol Process in Synthesis

  摘要：

  [GRAPHICS]The nonaldol aldol process developed in our laboratories has been applied to the synthesis of a C-1-C-11 fragment 22 of the novel macrocyclic cytotoxic agents tedanolide and 13-deoxytedanolide 1 and 2. The commercially available hydroxy ester 7 was converted in 24 steps into compound 22 using two nonaldol aldol reactions.

  DOI：

  10.1021/ol005675l

文献信息

• Use of the non-aldol aldol process in the synthesis of the C1–C11 fragment of the tedanolides: use of lactol ethers in place of tetrahydrofurans
  作者：Michael E Jung、Christopher P Lee

  DOI：10.1016/s0040-4039(00)01726-3

  日期：2000.12

  The use of a lactol methyl ether 23 in place of the simple tetrahydrofuran 11 allows for the high yielding non-aldol aldol process to occur without concomitant tetrahydropyran formation (cf 13) to give the desired product 24 in good yield. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Efficient Synthesis of the C₁−C₁₁ Fragment of the Tedanolides. The Nonaldol Aldol Process in Synthesis
  作者：Michael E. Jung、Rodolfo Marquez

  DOI：10.1021/ol005675l

  日期：2000.6.1

  [GRAPHICS]The nonaldol aldol process developed in our laboratories has been applied to the synthesis of a C-1-C-11 fragment 22 of the novel macrocyclic cytotoxic agents tedanolide and 13-deoxytedanolide 1 and 2. The commercially available hydroxy ester 7 was converted in 24 steps into compound 22 using two nonaldol aldol reactions.