(2S,3S)-3-Methyl-pentane-1,2-diol | 29117-58-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S)-3-Methyl-pentane-1,2-diol
• 英文别名: (2R,3S)-3-methyl-1,2-pentanediol；(2S,3S)-3-methylpentane-1,2-diol；(2s,3s)3-Methyl 1,2-pentanediol
• CAS: 29117-58-6
• 化学式: C₆H₁₄O₂
• 分子量: 118.176
• InChiKey: OGLLAZUAZSIDFE-NTSWFWBYSA-N

物化性质

• 沸点：
  60-61 °C(Press: 0.06 Torr)
• 密度：
  0.958±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 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：

  (2S,3S)-3-Methyl-pentane-1,2-diol 在 吡啶 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 (1R,2R)-1-Ethyl-2-methylbutylamin
  参考文献：
  名称：

  Kirmse, Wolfgang; Prolingheuer, Ernst-Christoph, Chemische Berichte, 1980, vol. 113, # 1, p. 104 - 128

  摘要：

  DOI：
• 作为产物：
  描述：

  L-异亮氨酸 在 lithium aluminium tetrahydride 、 氯化亚砜 、 硫酸 、 水 、 sodium nitrite 作用下， 以 乙醚 为溶剂， 反应 69.25h， 生成 (2S,3S)-3-Methyl-pentane-1,2-diol
  参考文献：
  名称：

  Synthesis of new chiral ionic liquids from α-hydroxycarboxylic acids

  摘要：

  New functionalized optically active N-methylimidazolium ionic liquids with an asymmetric center at the beta-position to the imdazole ring were synthesized as bromide salts from optically active alpha-hydroxycarboxylic acids. The bromide anions were exchanged by carboxylate anions with Amberlite IRA 400 ionic exchange resin. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.01.024

文献信息

• Facile Entry into Triazole Fused Heterocycles via Sulfamidate Derived Azido-alkynes
  作者：V. Sai Sudhir、N. Y. Phani Kumar、R. B Nasir Baig、Srinivasan Chandrasekaran

  DOI：10.1021/jo9016748

  日期：2009.10.2

  Direct synthesis of condensed triazoles from diverse sulfamidates by ring opening of sulfamidates with sodium azide followed by one-pot propargylation and cycloaddition furnished title compounds. The methodology in general has been demonstrated on diverse sulfamidates derived from amino acids, amino acid derivatives, and carbohydrates to obtain diverse triazole fused scaffolds. In one example, a condensed

  通过用叠氮化钠使氨基磺酸盐开环，然后进行一锅炔丙基化和环加成反应制得标题化合物，由多种氨基磺酸盐直接合成缩合三唑。一般而言，该方法论已在衍生自氨基酸，氨基酸衍生物和碳水化合物的多种氨基磺酸盐上得到了证明，从而获得了多种由三唑稠合而成的支架。在一个实例中，已经通过使磺酰胺酯衍生物与炔丙基胺开环合成了含氨基酸的稠合三唑。
• 1,2-Diastereoselective C-C Bond-Forming Reactions for the Synthesis of Chiral β-Branched α-Amino Acids
  作者：Thomas Spangenberg、Angèle Schoenfelder、Bernhard Breit、André Mann

  DOI：10.1002/ejoc.201000865

  日期：2010.11

  S N 2' sequences have been employed for the synthesis of β-branched α-amino acids using 1,2-diastereocontrol for forming C―C bonds. An oxazolidine fragment derived from Garner's aldehyde provides the handle for facial discrimination and acts as a masked amino acid functionality. This study encompasses directed and non-directed allylic substitution reactions. The stereocontrol of the oxazolidine appendage

  SN 2' 序列已用于合成 β-支链 α-氨基酸，使用 1,2-非对映控制形成 C-C 键。来自 Garner 醛的恶唑烷片段提供了面部识别的手柄，并充当了掩蔽的氨基酸功能。该研究包括定向和非定向烯丙基取代反应。还研究了末端烯烃加氢甲酰化过程中恶唑烷附属物的立体控制。公开了了解反应的非对映化学结果以及合成应用的努力。
• Total synthesis of protomycinolide iv
  作者：Masanori Honda、Tsutomu Katsuki、Masaru Yamaguchi

  DOI：10.1016/s0040-4039(01)91187-6

  日期：1984.1

  A 16-membered macrolide antibiotic, protomycinolide IV, was synthesized from two fragments to which the chirality was introduced by asymmetric epoxidation of the appropriately chosen allylic alcohols. A new synthesis of the Prelog-Djerassi lactonic acid from one of the intermediates of the synthesis was also carried out.

  16-元大环内酯抗生素，protomycinolide IV是从与手性是由适当选择的烯丙基醇的不对称环氧化引入两个片段合成。还从合成的中间体之一进行了新的Prelog-杰拉西内酯的合成。
• Synthesis of hyperolactones A and C
  作者：Toshihiko Ueki、Matsumi Doe、Yoshiki Morimoto、Takamasa Kinoshita、Rika Tanaka、Kazuo Yoshihara

  DOI：10.1002/jhet.5570380124

  日期：2001.1

  Hyperolactones A (1) and C (3) have been synthesized starting from (S)-malic acid by a straightforward route. The unique spirolactone skeleton was efficiently constructed by one-pot reaction as a key step. The absolute stereochemistry of hyperolactones was unambiguously established by this synthesis.

  高丙内酯A（1）和C（3）已通过简单的方法从（S）-苹果酸开始合成。通过一锅反应有效地构建了独特的螺内酯骨架，这是关键步骤。高内酯的绝对立体化学是通过这种合成方法明确建立的。
• Solid-phase synthesis of peptidomimetic oligomers with a phosphodiester backbone
  作者：Peishan Lin、A. Ganesan

  DOI：10.1016/s0960-894x(98)00064-x

  日期：1998.3

  An unnatural biopolymer is described in which amino acid side-chains are presented along a negatively charged phosphodiester backbone. For this purpose, a series of phosphoramidite monomers was prepared from chiral 1,2-diols. These were efficiently converted into oligomers using standard coupling conditions on an automated DNA synthesizer. (C) 1998 Elsevier Science Ltd. All rights reserved.