(S)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethan-1-ol | 93711-20-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethan-1-ol
• 英文别名: (2S,3S)-1,2-O-isopropylidenebutane-1,2,3-triol；(1S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol
• CAS: 93711-20-7
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: YJZDTHNWQIMGBF-WDSKDSINSA-N

物化性质

• 沸点：
  193.4±15.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethan-1-ol 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 苯 为溶剂， 反应 44.0h， 生成 (S)-2,2-dimethyl-4-[(S)-1-(4-phenylphenoxy)ethyl]-1,3-dioxolane
  参考文献：
  名称：

  Enantioselective synthesis of fatty acid amide hydrolase inhibitors with 1,3-disubstituted butan-2-one scaffold

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2017.02.013
• 作为产物：
  描述：

  ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate 在 lithium aluminium tetrahydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醚 、 苯 为溶剂， 反应 3.0h， 生成 (S)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethan-1-ol
  参考文献：
  名称：

  The chemistry of L-ascorbic and D-isoascorbic acids. 1. The preparation of chiral butanetriols and -tetrols

  摘要：

  DOI：

  10.1021/jo00246a037

文献信息

• Stem Cell Culture Methods
  申请人：Adams David Roger

  公开号：US20120202287A1

  公开（公告）日：2012-08-09

  The invention provides methods for reversibly inhibiting stem cell differentiation wherein a compound of formula (I) is contacted with a stem cell. The invention further provides a method for preparing a culture medium, a culture medium supplement and a composition comprising a compound of formula (I).

  该发明提供了一种可逆抑制干细胞分化的方法，其中将式(I)的化合物与干细胞接触。该发明还提供了一种制备培养基、培养基添加剂和包含式(I)化合物的组合物的方法。
• Practical enantiospecific syntheses of (+) erythro-9- (2s-hydroxy-3r-nonyl) adenine.
  作者：Elie Abushanab、Michel Bessodes、Kostas Antonakis

  DOI：10.1016/s0040-4039(01)91182-7

  日期：1984.1

  Three enantiospecific syntheses of 1S (2S-benzyloxethyl) oxirane (9) from L-ascorbic acid, L(+) tartaric acid, and Z-butene 1,4-diol are reported. The conversion of 9 to 2S-hydroxy-3R-nonylamine (19) is also described.

  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）。
• A convenient approach to total synthesis of synargentolide-B from l-ascorbic acid and d-ribose
  作者：Saidulu Konda、K. Bhaskar、Lingaiah Nagarapu、Dattatray M. Akkewar

  DOI：10.1016/j.tetlet.2014.03.133

  日期：2014.5

  A convenient and practical approach for the total synthesis of naturally occurring lactone synargentolide-B has been accomplished in 14 steps from the commercially available l-ascorbic acid and d-ribose involving Bestmann–Ohira reaction, zinc mediated allylation, ring closing-metathesis, and cross-metathesis reactions. The highlight of our strategy describes a one-pot reaction involving stereoselective

  对于天然存在的内酯synargentolide-B已经在14个步骤由市售完成了全合成的方便和实用的方法升抗坏血酸和ð核糖涉及Bestmann-大平反应，锌介导的烯丙基化，环闭合复分解反应，并跨复分解反应。我们策略的重点是描述一锅反应，包括立体选择性添加烯丙基锌试剂和选择性还原末端炔烃以获得关键的高级中间体。
• ABUSHANAB, ELIE;VEMISHETTI, PURUSHOTHAM;LEIBY, ROBERT W.;SINGH, HARIBINSH+, J. ORG. CHEM., 53,(1988) N 11, 2598-2602
  作者：ABUSHANAB, ELIE、VEMISHETTI, PURUSHOTHAM、LEIBY, ROBERT W.、SINGH, HARIBINSH+

  DOI：——

  日期：——
• US7410996B2
  申请人：——

  公开号：US7410996B2

  公开（公告）日：2008-08-12