methyl (1R,2S,3R)-3-tert-butyldimethylsilyloxy-2-(5-hydroxy-cis-2-pentenyl)-1-cyclopentaneacetate | 223448-38-2

• 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: methyl (1R,2S,3R)-3-tert-butyldimethylsilyloxy-2-(5-hydroxy-cis-2-pentenyl)-1-cyclopentaneacetate
• 英文别名: methyl 2-[(1R,2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[(Z)-5-hydroxypent-2-enyl]cyclopentyl]acetate
• CAS: 223448-38-2
• 化学式: C₁₉H₃₆O₄Si
• 分子量: 356.578
• InChiKey: LDGJZVZZZYESLE-VBHIHJPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (1R,2S,3R)-3-tert-butyldimethylsilyloxy-2-(5-hydroxy-cis-2-pentenyl)-1-cyclopentaneacetate 在 氢氟酸 、 氰化汞 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 5.5h， 生成 methyl (1R,2S)-3-oxo-2-(5-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy-cis-2-pentenyl)-1-cyclopentaneacetate
  参考文献：
  名称：

  Synthesis of both the enantiomers of methyl tuberonate, natural methyl β-d-glucopyranosyloxyjasmonate and its epimer

  摘要：

  Synthesis of both the enantiomers of methyl tuberonate 3, natural methyl beta-D-glucopyranosyloxyjasmonate 6, and its epimer, methyl beta-D-glucopyranosyl-tuberonate 5 is described. They were synthesized via mild deprotection of dichloroacetate and trifluoroacetate by methanolysis from the enantiomerically pure dithiane 9. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00157-x
• 作为产物：
  描述：

  2-((1R,2S,3R)-3-hydroxy-2-((Z)-5-(tetrahydro-2H-pyran-2-yloxy)pent-2-enyl)cyclopentyl)ethanoic acid 在 咪唑 、 二甲基氯化铝 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 methyl (1R,2S,3R)-3-tert-butyldimethylsilyloxy-2-(5-hydroxy-cis-2-pentenyl)-1-cyclopentaneacetate
  参考文献：
  名称：

  Synthesis of both the enantiomers of methyl tuberonate, natural methyl β-d-glucopyranosyloxyjasmonate and its epimer

  摘要：

  Synthesis of both the enantiomers of methyl tuberonate 3, natural methyl beta-D-glucopyranosyloxyjasmonate 6, and its epimer, methyl beta-D-glucopyranosyl-tuberonate 5 is described. They were synthesized via mild deprotection of dichloroacetate and trifluoroacetate by methanolysis from the enantiomerically pure dithiane 9. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00157-x

文献信息

• Enantioselective Synthesis of Both the Enantiomers of Jasmine Ketolactone and Its Epimer
  作者：Munenori INOUE、Tsunehiro NISHI、Takeshi KITAHARA

  DOI：10.1271/bbb.63.1122

  日期：1999.1

  The enantioselective synthesis of jasmine ketolactone 1, which was isolated as a component of Italian jasmine oil, and its epimer 2 is described. Lactones 1 and 2 were synthesized in 5 and 4 steps, respectively, by Yamaguchi's macrolactonization method from alcohol 4.

  描述了作为意大利茉莉油成分的茉莉酮酮内酯1的对映选择性合成及其差向异构体2。内酯1和2分别通过Yamaguchi的大环内酯化法从乙醇4分5步和4步合成。
• Synthesis of both the enantiomers of methyl tuberonate, natural methyl β-d-glucopyranosyloxyjasmonate and its epimer
  作者：Munenori Inoue、Takeshi Kitahara

  DOI：10.1016/s0040-4020(99)00157-x

  日期：1999.4

  Synthesis of both the enantiomers of methyl tuberonate 3, natural methyl beta-D-glucopyranosyloxyjasmonate 6, and its epimer, methyl beta-D-glucopyranosyl-tuberonate 5 is described. They were synthesized via mild deprotection of dichloroacetate and trifluoroacetate by methanolysis from the enantiomerically pure dithiane 9. (C) 1999 Elsevier Science Ltd. All rights reserved.