(R)-5-Benzyloxy-3-trimethylsilanyloxy-pentanoic acid ethyl ester | 309755-11-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-5-Benzyloxy-3-trimethylsilanyloxy-pentanoic acid ethyl ester
• CAS: 309755-11-1
• 化学式: C₁₇H₂₈O₄Si
• 分子量: 324.492
• InChiKey: UPJRUODAJHUDIX-MRXNPFEDSA-N

物化性质

• 沸点：
  365.7±37.0 °C(predicted)
• 密度：
  1.004±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  22.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-5-Benzyloxy-3-trimethylsilanyloxy-pentanoic acid ethyl ester 在 偶氮二异丁腈 、 (R)-oxazaborolidinone derived from BH₃*THF 、 N-对甲苯磺酰基-D-缬氨酸 、 三正丁基氢锡 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 (3S,5R)-7-Benzyloxy-3-hydroxy-5-trimethylsilanyloxy-heptanoic acid ethyl ester
  参考文献：
  名称：

  An effective extension of the polyacetate chain in the polyene macrolide antibiotic filipin III, based on chiral oxazaborolidinone-promoted asymmetric aldol reactions

  摘要：

  The enantioselective construction of the iterative polyacetate unit 3 in filipin III has been accomplished, essentially by an aldol strategy based on chiral oxazaborolidinone-promoted asymmetric aldol reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01289-2
• 作为产物：
  描述：

  ethyl 2-[(1R)-1-hydroxy-3-phenylmethoxypropyl]-1,3-dithiolane-2-carboxylate 在 2,6-二甲基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 生成 (R)-5-Benzyloxy-3-trimethylsilanyloxy-pentanoic acid ethyl ester
  参考文献：
  名称：

  An effective extension of the polyacetate chain in the polyene macrolide antibiotic filipin III, based on chiral oxazaborolidinone-promoted asymmetric aldol reactions

  摘要：

  The enantioselective construction of the iterative polyacetate unit 3 in filipin III has been accomplished, essentially by an aldol strategy based on chiral oxazaborolidinone-promoted asymmetric aldol reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01289-2

文献信息

• Formal Synthesis of (−)-Apicularen A
  作者：Benjamin R. Graetz、Scott D. Rychnovsky

  DOI：10.1021/ol0353417

  日期：2003.9.1

  [GRAPHICS]A formal synthesis of (-)-apicularen A has been completed. The synthesis features a cyanohydrin acetonide coupling as a convergent approach to the C9-C18 segment and an intramolecular Diels-Alder addition sequence to create both the 10-membered macrocycle and the aromatic ring.
• Empirical Model for the Molar Rotations of <i>syn</i>-2,2-Dimethyl-1,3-dioxanes
  作者：Christopher D. Anderson、Scott D. Rychnovsky

  DOI：10.1021/ol0263550

  日期：2002.9.1

  [GRAPHICS]A useful method for the prediction of molar rotation ([Phi]) of syn-2,2-dimethyl-1,3-dioxanes (acetonides) is described. A series of acetonides were prepared by standard methods. A simple additive relationship between the substituents (R, R') and molar rotation was realized.