-3,4-<(1-methylethyliden)bis(oxy)>butandiol-4-(methylbenzolsulfonat) | 128990-14-7

• 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: -3,4-<(1-methylethyliden)bis(oxy)>butandiol-4-(methylbenzolsulfonat)
• 英文别名: 1,2-O-Isopropylidene-4-O-(4-toluenesulfonyl)-D-threitol；(S)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl4-methylbenzenesufonate；(2S,3S)-2-hydroxy-3,4-isopropylidenedioxy-1-(p-toluenesulfonyloxy)-butane
• CAS: 128990-14-7；135577-94-5；142470-85-7；93367-09-0
• 化学式: C₁₄H₂₀O₆S
• 分子量: 316.375
• InChiKey: FBWZULOKFBROIR-STQMWFEESA-N

物化性质

• 沸点：
  461.9±35.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.21
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  82.06
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  -3,4-<(1-methylethyliden)bis(oxy)>butandiol-4-(methylbenzolsulfonat) 在 sodium methylate 作用下， 以 乙醚 为溶剂， 生成 (2S,3S)-3,4-epoxy-1,2-di-O-isopropylidenebutane-1,2-diol
  参考文献：
  名称：

  实用的对映体特异性合成（+）erythro-9-（2s-hydroxy-3r-nonyl）腺嘌呤。

  摘要：

  报道了从L-抗坏血酸，L（+）酒石酸和Z-丁烯1,4-二醇合成1S（2S-苄氧基乙基）环氧乙烷（9）的三种对映体特异性化合物。还描述了从9到2S-羟基-3R-壬胺的转化（19）。

  DOI：

  10.1016/s0040-4039(01)91182-7
• 作为产物：
  描述：

  3,4-O-异亚丙基-L-苏糖酸甲酯 在 lithium aluminium tetrahydride 作用下， 以 吡啶 为溶剂， 生成 -3,4-<(1-methylethyliden)bis(oxy)>butandiol-4-(methylbenzolsulfonat)
  参考文献：
  名称：

  实用的对映体特异性合成（+）erythro-9-（2s-hydroxy-3r-nonyl）腺嘌呤。

  摘要：

  报道了从L-抗坏血酸，L（+）酒石酸和Z-丁烯1,4-二醇合成1S（2S-苄氧基乙基）环氧乙烷（9）的三种对映体特异性化合物。还描述了从9到2S-羟基-3R-壬胺的转化（19）。

  DOI：

  10.1016/s0040-4039(01)91182-7

文献信息

• Ti(iii)-mediated radical cyclization of epoxy-β-aminoacrylate in the synthesis of the substituted pyrrolidine core of necine bases: synthesis of 2-epi-rosmarinecine
  作者：Sandip Basu、Pancham S. Kandiyal、Ravi Sankar Ampapathi、Tushar Kanti Chakraborty

  DOI：10.1039/c3ra42315h

  日期：——

  A radical-mediated approach to the necine base 2-epi-rosmarinecine is described. The synthesis is based on the stereoselective formation of a highly substituted pyrrolidine ring from β-aminoacrylate, diastereoselective allylation and intramolecular cyclization.

  描述了一种针对烟碱2-表位-迷迭香碱的自由基介导的方法。该合成基于β-氨基丙烯酸酯立体选择性形成高度取代的吡咯烷环，非对映选择性烯丙基化和分子内环化。
• A short, simple and general approach for the synthesis of (3S,4S)-3-methoxy-4-methylamino pyrrolidine and (3S,4R)-3-methoxy-4-methylamino pyrrolidine
  作者：A.Ravi Kumar、J.Santhosh Reddy、B.Venkateswara Rao

  DOI：10.1016/s0040-4039(03)01362-5

  日期：2003.7

  A general and efficient stereoselective approach for the synthesis of (3S,4S) and (3S,4R)-3-methoxy-4-methylamino pyrrolidines, a part of the structure of AG-7352, a naphthyridine antitumor agent and quinoline antibacterial compounds has been described.

  合成（3 S，4 S）和（3 S，4 R）-3-甲氧基-4-甲基氨基吡咯烷酮，AG-7352结构的一部分，萘啶类抗肿瘤药和已经描述了喹啉抗菌化合物。
• First stereoselective total synthesis of panaxjapyne C
  作者：Pallavi Thakur、B. Kumaraswamy、G. Raji Reddy、Rakeshwar Bandichhor、K. Mukkanti

  DOI：10.1016/j.tetlet.2012.04.087

  日期：2012.7

  The first stereoselective total synthesis of polyacetylene panaxjapyne C is described. The key reactions include regioselective opening of the epoxide and Cadiot–Chodkiewicz cross-coupling reactions. l-Ascorbic acid was used as a chiral pool material for the construction of the both terminal acetylenes.

  描述了聚乙炔人参ja啶C的第一立体选择性全合成。关键反应包括环氧化物的区域选择性开放和Cadiot-Chodkiewicz交叉偶联反应。1-抗坏血酸用作两个末端乙炔的手性池材料。
• Enantioselective synthesis of fatty acid amide hydrolase inhibitors with 1,3-disubstituted butan-2-one scaffold
  作者：Tom R. Sundermann、Matthias Lehr

  DOI：10.1016/j.tetasy.2017.02.013

  日期：2017.3

  Fatty acid amide hydrolase is a key enzyme in the inactivation of the analgesic and anti-inflammatory endocannabinoid anandamide. Previously, the chiral compound 1-(1H-benzotriazol-1-y1)-3-(4phenylphenoxy)butan-2-one was identified as a potent inhibitor of fatty acid amide hydrolase and is therefore of interest as a potential agent against pain and inflammation. Two different approaches for the enantioselective synthesis of fatty acid amide hydrolase inhibitors with a 1,3-disubstituted butan2-one scaffold were carried out. The first one uses the chiral epoxide 2-[1-(4-phenylphenoxy)ethylloxirane with an (R)- or (S)-configuration at the exocyclic stereocenter as central intermediates. These substances were obtained by separation of the non-stereoselectively synthesized epoxide into its racemic diastereomers by reversed phase chromatography followed by Jacobsen's hydrolytic kinetic resolution of each enantiomer with the (S)-configured oxirane ring. Furthermore, a chiral pool based enantioselective synthesis was developed. In that case, the starting compound for both target enantiomers was methyl 3,4-0-isopropylidene-L-threonate. In comparison to the first approach, the chiral pool synthesis consisted of more steps, but generated the enantiomers with much better enantiomeric excess. Biological evaluation showed that the (R)-enantiomer inhibits isolated fatty acid amide hydrolase with a 200-fold higher activity than the (S)-enantiomer. (C) 2017 Elsevier Ltd. All rights reserved.
• Stereoselective total synthesis of microcarpalide
  作者：G.V.M. Sharma、Govardhan R. Cherukupalli

  DOI：10.1016/j.tetasy.2006.03.024

  日期：2006.4

  A stereoselective total synthesis of microcarpalide using ring-closing metathesis (RCM) as a key step is reported. L-Ascorbic acid was used as a chiral pool material for the construction of the olefinic alcohol and an asymmetric aldol reaction provided the chiral precursor for the synthesis of olefinic acid. (c) 2006 Elsevier Ltd. All rights reserved.