((2R,6S)-6-allyltetrahydropyran-2-yl)acetic acid ethyl ester | 866021-62-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: ((2R,6S)-6-allyltetrahydropyran-2-yl)acetic acid ethyl ester
• 英文别名: ethyl 2-((2R,6S)-6-allyltetrahydro-2H-pyran-2-yl)acetate；ethyl 2-[(2R,6S)-6-prop-2-enyloxan-2-yl]acetate
• CAS: 866021-62-7
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: FVXMFAPHAAPSDI-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ((2R,6S)-6-allyltetrahydropyran-2-yl)acetic acid ethyl ester 在 palladium hydroxide - carbon 咪唑 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氢气 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 臭氧 、 溶剂黄146 、 三乙胺 、 (-)-diisopinocamphenylborane chloride 、 tetramethylammonium triacetoxyborohydride 作用下， 以 乙醚 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (R)-2-[(4R,6R)-6-((R)-2-(tert-butyldimethylsilanyloxy)-3-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}propyl)-2,2-dimethyl-[1,3]dioxan-4-yl]propionaldehyde
  参考文献：
  名称：

  Toward the Synthesis of Spirastrellolide A:  Construction of Two C₁−C₂₅ Diastereomers Containing the BC−Spiroacetal

  摘要：

  Stereocontrolled syntheses of two possible C-1-C-25 diastereomers of spirastrellolide A containing the cis-disubstituted tetrahydropyran and [6,6]-spiroacetal are reported, exploiting boron-mediated asymmetric aldol and allylation methodology.

  DOI：

  10.1021/ol051405x
• 作为产物：
  描述：

  (E)-(S)-7-hydroxydeca-2,9-dienoic acid ethyl ester 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到((2R,6S)-6-allyltetrahydropyran-2-yl)acetic acid ethyl ester
  参考文献：
  名称：

  Toward the Synthesis of Spirastrellolide A:  Construction of Two C₁−C₂₅ Diastereomers Containing the BC−Spiroacetal

  摘要：

  Stereocontrolled syntheses of two possible C-1-C-25 diastereomers of spirastrellolide A containing the cis-disubstituted tetrahydropyran and [6,6]-spiroacetal are reported, exploiting boron-mediated asymmetric aldol and allylation methodology.

  DOI：

  10.1021/ol051405x

文献信息

• TBAF-catalyzed cyclization of 6-hydroxyhex-2-ynoates and 7-hydroxyhept-2-ynoates
  作者：Xiao Qing Wang、Ping Jing Jia、Su Ping Liu、Wei Yu

  DOI：10.1016/j.cclet.2011.01.023

  日期：2011.8

  Tetrabutyl ammonium fluoride (TBAF) was found to be capable of catalyzing the intramolecular hydroalkoxylation of 6-hydroxyhex-2-ynoates and 7-hydroxyhept-2-ynoates. The reaction could be used to prepare 2,5-substituted THF rings and 2,6-substituted THP rings. (C) 2011 Wei Yu. Published by Elsevier BY, on behalf of Chinese Chemical Society. All rights reserved.
• Toward the stereoselective synthesis of C1–C23 fragment of spirastrellolide B
  作者：Akkapalli Rajesh、Gangavaram V.M. Sharma、Krishna Damera

  DOI：10.1016/j.tetlet.2014.05.111

  日期：2014.7

  A convergent synthesis of the protected C(1)-C(23) fragment 4 of the targeted natural product spirast-rellolide B is described. The key step of the synthesis is cross metathesis (CM) and TBAF promoted oxa-Michael to construct tetrahydropyran moiety. (C) 2014 Elsevier Ltd. All rights reserved.
• Toward the Synthesis of Spirastrellolide A:  Construction of Two C₁−C₂₅ Diastereomers Containing the BC−Spiroacetal
  作者：Ian Paterson、Edward A. Anderson、Stephen M. Dalby、Olivier Loiseleur

  DOI：10.1021/ol051405x

  日期：2005.9.1

  Stereocontrolled syntheses of two possible C-1-C-25 diastereomers of spirastrellolide A containing the cis-disubstituted tetrahydropyran and [6,6]-spiroacetal are reported, exploiting boron-mediated asymmetric aldol and allylation methodology.