(E)-(1,2:5,6-di-O-isopropylidene-D-glucofuranose-3-O-yl) 2-methyl-2-decenoate

• 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: (E)-(1,2:5,6-di-O-isopropylidene-D-glucofuranose-3-O-yl) 2-methyl-2-decenoate
• 英文别名: [(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] (E)-2-methyldec-2-enoate
• 化学式: C₂₃H₃₈O₇
• 分子量: 426.551
• InChiKey: YKOQTTHQFAIJMH-WKNIDMHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-(1,2:5,6-di-O-isopropylidene-D-glucofuranose-3-O-yl) 2-methyl-2-decenoate 在 六甲基磷酰三胺 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 (2R)-(1,2:5,6-di-O-isopropylidene-D-glucofuranose-3-O-yl) (Z)-2-methyl-3-decenoate 、 (2R)-(1,2:5,6-di-O-isopropylidene-D-glucofuranose-3-O-yl) (E)-2-methyl-3-decenoate
  参考文献：
  名称：

  Anionic versus photochemical diastereoselective deconjugation of diacetone d-glucose α,β-unsaturated esters

  摘要：

  Deconjugation of diacetone D-glucose alpha, beta-unsaturated esters has been conducted by deprotonation using NaHMDS with HMPA as co-solvent followed by stereoselective protonation at low temperature. High selectivities (>95%) were obtained with oc-methyl linear compounds. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00365-3
• 作为产物：
  描述：

  2-甲基癸-2-烯酸 、 双丙酮葡萄糖 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以73%的产率得到(E)-(1,2:5,6-di-O-isopropylidene-D-glucofuranose-3-O-yl) 2-methyl-2-decenoate
  参考文献：
  名称：

  Anionic versus photochemical diastereoselective deconjugation of diacetone d-glucose α,β-unsaturated esters

  摘要：

  Deconjugation of diacetone D-glucose alpha, beta-unsaturated esters has been conducted by deprotonation using NaHMDS with HMPA as co-solvent followed by stereoselective protonation at low temperature. High selectivities (>95%) were obtained with oc-methyl linear compounds. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00365-3

文献信息

• Anionic versus photochemical diastereoselective deconjugation of diacetone d-glucose α,β-unsaturated esters
  作者：Frédéric Bargiggia、Olivier Piva

  DOI：10.1016/s0957-4166(03)00365-3

  日期：2003.7

  Deconjugation of diacetone D-glucose alpha, beta-unsaturated esters has been conducted by deprotonation using NaHMDS with HMPA as co-solvent followed by stereoselective protonation at low temperature. High selectivities (>95%) were obtained with oc-methyl linear compounds. (C) 2003 Elsevier Science Ltd. All rights reserved.