(3R,4S)-4-Benzyloxymethoxy-5-(tert-butyl-diphenyl-silanyloxy)-3-phenyl-pentanoic acid methyl ester | 234433-82-0

• 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: (3R,4S)-4-Benzyloxymethoxy-5-(tert-butyl-diphenyl-silanyloxy)-3-phenyl-pentanoic acid methyl ester
• 英文别名: methyl (3R,4S)-5-[tert-butyl(diphenyl)silyl]oxy-3-phenyl-4-(phenylmethoxymethoxy)pentanoate
• CAS: 234433-82-0
• 化学式: C₃₆H₄₂O₅Si
• 分子量: 582.812
• InChiKey: IFACVXCNRKYVAJ-KKLWWLSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.47
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4S)-4-Benzyloxymethoxy-5-(tert-butyl-diphenyl-silanyloxy)-3-phenyl-pentanoic acid methyl ester 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (E)-(4R,5R)-4-Benzyloxymethoxy-7-hydroxy-5-phenyl-hept-2-enoic acid methyl ester
  参考文献：
  名称：

  One- and two-directional iterative 1,2-asymmetric induction in acyclic systems—easy access to anti,anti and anti,syn dipropionate and diphenylacetate stereotriads

  摘要：

  Stereocontrolled addition of organocuprate reagents to gamma-alkoxy-alpha,beta-unsaturated esters can be done in one- and two-directional modes with excellent 1,2-induction. Enolate hydroxylations proceed with high diastereoselectivity affording acyclic chains with three to five contiguous stereogenic centers of the propionate and phenylpropionate triad types. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00783-2
• 作为产物：
  描述：

  phenylmagnesium bromide 、 Methyl (4S,E)-4-(benzyloxymethoxy)-5-(tert-butyldiphenylsiloxy)-2-pentenoate 在 copper(l) iodide 、 三甲基氯硅烷 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到(3R,4S)-4-Benzyloxymethoxy-5-(tert-butyl-diphenyl-silanyloxy)-3-phenyl-pentanoic acid methyl ester
  参考文献：
  名称：

  One- and two-directional iterative 1,2-asymmetric induction in acyclic systems—easy access to anti,anti and anti,syn dipropionate and diphenylacetate stereotriads

  摘要：

  Stereocontrolled addition of organocuprate reagents to gamma-alkoxy-alpha,beta-unsaturated esters can be done in one- and two-directional modes with excellent 1,2-induction. Enolate hydroxylations proceed with high diastereoselectivity affording acyclic chains with three to five contiguous stereogenic centers of the propionate and phenylpropionate triad types. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00783-2

文献信息

• From glyceraldehyde to functionalized enantiopure tetrahydronaphthalenes and indanes
  作者：Stephen Hanessian、Jianguo Ma

  DOI：10.1016/s0040-4039(01)01914-1

  日期：2001.12

  Tricyclic tetrahydronaphthalenes comprising cis- and trans-fused lactones, and aryl substituted functionalized indanes were synthesized in enantiopure form.

  以对映纯形式合成了包含顺式和反式内酯的三环四氢萘以及芳基取代的官能化茚满。
• One- and two-directional iterative 1,2-asymmetric induction in acyclic systems—easy access to anti,anti and anti,syn dipropionate and diphenylacetate stereotriads
  作者：Stephen Hanessian、Jianguo Ma、Wengui Wang

  DOI：10.1016/s0040-4039(99)00783-2

  日期：1999.6

  Stereocontrolled addition of organocuprate reagents to gamma-alkoxy-alpha,beta-unsaturated esters can be done in one- and two-directional modes with excellent 1,2-induction. Enolate hydroxylations proceed with high diastereoselectivity affording acyclic chains with three to five contiguous stereogenic centers of the propionate and phenylpropionate triad types. (C) 1999 Elsevier Science Ltd. All rights reserved.