(3S,4R)-3-methyl-1,4-pentanediol | 184104-11-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4R)-3-methyl-1,4-pentanediol
• 英文别名: (3S,4R)-3-methylpentane-1,4-diol
• CAS: 184104-11-8
• 化学式: C₆H₁₄O₂
• 分子量: 118.176
• InChiKey: WOHXXIWTEHLCQK-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-methyl-1,4-pentanediol 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 lithium hydroxide 、 草酰氯 、 camphor-10-sulfonic acid 、 氢氟酸 、 ammonium acetate 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 水 、 sodium hydride 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  海洋来源的具有细胞毒性的35元环二肽dolastatin G和nordolastatin G的合成

  摘要：

  从日本野兔Dolabella auricularia合成新的细胞毒性环肽肽dolastatin G（1）和nordolastatin G（2），是对映选择性的，目前的结果明确证实了它们的立体结构。

  DOI：

  10.1016/0040-4039(96)01653-x
• 作为产物：
  描述：

  (+/-)-3-methyl-1,4-pentanediol 在 lithium aluminium tetrahydride 、 novozyme 435 、 甲基叔丁基醚 作用下， 以 乙醚 为溶剂， 反应 72.5h， 生成 (3S,4R)-3-methyl-1,4-pentanediol
  参考文献：
  名称：

  Synthesis of diastereo- and enantiomerically pure anti-3-methyl-1,4-pentanediol via lipase catalysed acylation

  摘要：

  Racemic trans-4,5-dimethylhydrofuran-2(3H)-one was synthesised from 5-methyl-furan-2(3H)-one, (alpha-angelica lactone). The key reaction in the synthesis was the 1,4-conjugate addition of an organocuprate to 5-methylfuran-2(5H)-one (beta-angelica lactone). Different types of organocuprates were tested with the highest anti:syn ratio of 99.4:0.6 being obtained by the use of a Gilman organocuprate reagent. The enantioselective acylation of racemic 3-methyl-pentan-1,4-diol, catalysed by a variety of lipases in organic media, was investigated. The highest enantioselectivity (E > 400) was obtained when Novozyme 435 was used as the catalyst at a water activity of a(w) similar to 0. Thus, both enantiomers, (3S,4R)- and (3R,4S)-3-methyl-pentan-1,4-diol, were obtained in very high diastereomeric (> 99% de) and enantiomeric purities (> 99.8% and > 97.4% ee, respectively). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.043

文献信息

• Synthesis of dolastatin G and nordolastatin G, cytotoxic 35-membered cyclodepsipeptides of marine origin
  作者：Tsuyoshi Mutou、Takashi Kondo、Takunobu Shibata、Makoto Ojika、Hideo Kigoshi、Kiyoyuki Yamada

  DOI：10.1016/0040-4039(96)01653-x

  日期：1996.9

  The synthesis of dolastatin G (1) and nordolastatin G (2), new cytotoxic cyclodepsipeptides from the Japanese sea hare Dolabella auricularia, was achieved enantioselectively, and the present result confirmed their stereostructures unambiguously.

  从日本野兔Dolabella auricularia合成新的细胞毒性环肽肽dolastatin G（1）和nordolastatin G（2），是对映选择性的，目前的结果明确证实了它们的立体结构。
• Synthesis of diastereo- and enantiomerically pure anti-3-methyl-1,4-pentanediol via lipase catalysed acylation
  作者：Mona Lindström、Erik Hedenström、Sandrine Bouilly、Kelly Velonia、Ioulia Smonou

  DOI：10.1016/j.tetasy.2005.01.043

  日期：2005.4

  Racemic trans-4,5-dimethylhydrofuran-2(3H)-one was synthesised from 5-methyl-furan-2(3H)-one, (alpha-angelica lactone). The key reaction in the synthesis was the 1,4-conjugate addition of an organocuprate to 5-methylfuran-2(5H)-one (beta-angelica lactone). Different types of organocuprates were tested with the highest anti:syn ratio of 99.4:0.6 being obtained by the use of a Gilman organocuprate reagent. The enantioselective acylation of racemic 3-methyl-pentan-1,4-diol, catalysed by a variety of lipases in organic media, was investigated. The highest enantioselectivity (E > 400) was obtained when Novozyme 435 was used as the catalyst at a water activity of a(w) similar to 0. Thus, both enantiomers, (3S,4R)- and (3R,4S)-3-methyl-pentan-1,4-diol, were obtained in very high diastereomeric (> 99% de) and enantiomeric purities (> 99.8% and > 97.4% ee, respectively). (c) 2005 Elsevier Ltd. All rights reserved.