(3S)-1,3-O-(1-methylethylidene)-5-O-(phenylmethyl)-1,3,5-pentanetriol | 164649-96-1

• 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: (3S)-1,3-O-(1-methylethylidene)-5-O-(phenylmethyl)-1,3,5-pentanetriol
• 英文别名: (4S)-4-[2-(Benzyloxy)ethyl]-2,2-dimethyl-1,3-dioxane；(4S)-2,2-dimethyl-4-(2-phenylmethoxyethyl)-1,3-dioxane
• CAS: 164649-96-1
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: JKLSLDYXJULKDK-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S)-1,3-O-(1-methylethylidene)-5-O-(phenylmethyl)-1,3,5-pentanetriol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 (4'R)-(-)-2-(2,2-Dimethyl-1,3-dioxan-4-yl)acetaldehyde
  参考文献：
  名称：

  Synthesis and absolute stereochemistry of the acyl moiety of quillajasaponins

  摘要：

  The acyl moiety of the quillajasaponins, one of the most important immunological adjuvants, was determined to be 3-(S), 5-(S)-dihydroxy-6-(S)-methyl-octanoic acid by enantioselective synthesis. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02124-3
• 作为产物：
  描述：

  (2E)-5-(苯基甲氧基)-2-戊烯-1-醇 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二乙酯 、 对甲苯磺酸 、 红铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (3S)-1,3-O-(1-methylethylidene)-5-O-(phenylmethyl)-1,3,5-pentanetriol
  参考文献：
  名称：

  Synthesis and absolute stereochemistry of the acyl moiety of quillajasaponins

  摘要：

  The acyl moiety of the quillajasaponins, one of the most important immunological adjuvants, was determined to be 3-(S), 5-(S)-dihydroxy-6-(S)-methyl-octanoic acid by enantioselective synthesis. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02124-3

文献信息

• Stereochemical Determination of Roflamycoin: 13C Acetonide Analysis and Synthetic Correlation
  作者：Scott D. Rychnovsky、George Griesgraber、Rolf Schlegel

  DOI：10.1021/ja00106a024

  日期：1995.1

  The relative configuration of natural roflamycoin (1) was determined by C-13 acetonide analysis, combined with other supporting spectroscopic data. A previous proposal for the configuration of roflamycoin was shown to be incorrect. The absolute configuration was determined by the advanced Mosher's method. Our proposed structure of natural roflamycoin was confirmed by the synthesis of a degradation fragment that incorporates all of the 11 independent stereogenic centers of roflamycoin. The complete structure of roflamycoin is illustrated in Figure 1.
• Synthesis and absolute stereochemistry of the acyl moiety of quillajasaponins
  作者：Xiangming Zhu、Biao Yu、Yongzheng Hui、Ryuichi Higuchi、Takanori Kusano、Tomofumi Miyamoto

  DOI：10.1016/s0040-4039(99)02124-3

  日期：2000.1

  The acyl moiety of the quillajasaponins, one of the most important immunological adjuvants, was determined to be 3-(S), 5-(S)-dihydroxy-6-(S)-methyl-octanoic acid by enantioselective synthesis. (C) 2000 Elsevier Science Ltd. All rights reserved.