(R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol | 165524-52-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol
• 英文别名: (1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol
• CAS: 165524-52-7
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: YJZDTHNWQIMGBF-RITPCOANSA-N

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：

  (R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium hydride 、 potassium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 、 2-甲基四氢呋喃 、 1,4-二氧六环 、 mineral oil 为溶剂， 反应 21.33h， 生成 N-(6-((R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethoxy)-2-(4-fluorobenzyl-thio)pyrimidin-4-yl)-3-methylazetidine-1-sulfonamide
  参考文献：
  名称：

  [EN] N- (6- ( (2R,3S) -3,4-DIHYDROXYBUTAN-2-YLOXY) -2- (4 - FLUOROBENZYLTHIO) PYRIMIDIN- 4 - YL) -3- METHYLAZETIDINE- 1 - SULFONAMIDE AS CHEMOKINE RECEPTOR MODULATOR
  [FR] N-(6-((2R,3S)-3,4-DIHYDROXYBUTAN-2-YLOXY)-2-(4-FLUOROBENZYLTHIO) PYRIMIDIN-4-YL)-3-METHYLAZETIDINE-1-SULFONAMIDE UTILISÉ EN TANT QUE MODULATEUR DU RÉCEPTEUR DE CHIMIOKINE

  摘要：

  提供了一种化合物，该化合物是（a）式（I）的嘧啶磺胺或（b）其药用可接受盐，该化合物的晶型，获得该化合物的过程，用于制造该化合物的药用中间体，以及含有该化合物的药物组合物。该化合物在治疗需要调节趋化因子受体活性有益的疾病/症状中有用。

  公开号：

  WO2013008002A1
• 作为产物：
  描述：

  (2S,3S)-3,4-epoxy-1,2-di-O-isopropylidenebutane-1,2-diol 在 lithium aluminium tetrahydride 、 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 24.33h， 生成 (R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol
  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
• 作为试剂：
  描述：

  (R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol 、 2-(2,3-difluorobenzylmercapto)-4,6-dichloropyrimidine 在 (R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol 作用下， 生成 4-chloro-2-[(2,3-difluorobenzyl)thio]-6-{(1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethoxy}pyrimidine
  参考文献：
  名称：

  Pyrimidine sulphonamide derivatives as chemokine receptor modulators

  摘要：

  公式（I）化合物，或其药学上可接受的盐，溶剂或体内可水解酯，以及包括这些化合物的药物组合物，均用于治疗趋化因子介导的疾病和障碍。

  公开号：

  US08722883B2

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。
• [EN] CXCR-2 INHIBITORS FOR TREATING CRYSTAL ARTHROPATHY DISORDERS<br/>[FR] INHIBITEURS DU CXCR-2 PERMETTANT DE TRAITER DES TROUBLES ASSOCIÉS À UNE ARTHROPATHIE CRISTALLINE
  申请人：ARDEA BIOSCIENCES INC

  公开号：WO2017156270A1

  公开（公告）日：2017-09-14

  N-(2-((2,3-difluorobenzyl)thio)-6-(((2R,3S)-3,4-dihydroxybutan-2-yl)oxy)pyrimidin-4-yl)azetidine-1-sulfonamide (compound 3) and N-(6-(((2R,3S)-3,4-dihydroxy butan-2-yl)oxy)-2-((4-fluoro benzyl)thio)pyrimidin-4-yl)-3-methylazetidine-1-sulfonamide(compound 4) are known chemokine modulators and are therefore useful in the treatment of diseases/conditions in which modulation of chemokine receptor activity is beneficial. In particular, provided herein are compositions and methods for the treatment and prevention of gout.

  N-(2-((2,3-二氟苄基)硫基)-6-(((2R,3S)-3,4-二羟基丁-2-基)氧基)嘧啶-4-基)氮杂环丙磺酰胺（化合物3）和N-(6-(((2R,3S)-3,4-二羟基丁-2-基)氧基)-2-((4-氟苄基)硫基)嘧啶-4-基)-3-甲基氮杂环丙磺酰胺（化合物4）是已知的化学调节剂，因此在调节趋化因子受体活性有益的疾病/症状的治疗中很有用。特别提供了用于痛风的治疗和预防的组合物和方法。
• CRYSTALLINE FORMS OF N-[2-[[(2,3-DIFLUOROPHENYL)METHYL]THIO]-6--4-PYRIMIDINYL]-1-AZETIDINESULFONAMIDE
  申请人：Gullberg Britt Anne Ingela

  公开号：US20120015927A1

  公开（公告）日：2012-01-19

  There is provided crystalline forms of N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1R,2S)-2,3-dihydroxy-1-methylpropyl]oxy}-4-pyrimidinyl]1-azetidinesulfon-amide anhydrate. Such compounds/forms may be useful in the treatment of a disease/condition in which modulation of chemokine receptor activity is beneficial.

  提供了N-[2-[[(2,3-二氟苯基)甲基]硫]-6-[(1R,2S)-2,3-二羟基-1-甲基丙基]氧基}-4-嘧啶基]1-氮杂环磺酰胺无水晶形态。这种化合物/形态可能在调节趋化因子受体活性有益的疾病/病症治疗中有用。
• Synthesis of (2R,3S)-1,2,3-Butanetriol Derivatives From (R)-2,3-O-Isopropylideneglyceraldehyde and of the (2S,3R)-Enantiomers FromD-Glucose. Application to the Synthesis of Enantiomerically Pure Muscarine
  作者：Johann Mulzer、Alfred Angermann、Winfried Münch、Günter Schlichthörl、Angelo Hentzschel

  DOI：10.1002/jlac.198719870103

  日期：1987.1.31

  Both enantiomers of the O-protected epoxy alcohol derivative 1b have been prepared from (R)-2,3-O-isopropylideneglyceraldehyde and D-glucose, respectively, and utilized in a practical synthesis of L- and D-muscarine iodide and chloride.

  O-保护的环氧醇衍生物1b的两种对映体分别由（R）-2，3 - O-异亚丙基甘油醛和D-葡萄糖制备，并用于L-和D-穆斯卡因碘化物和氯化物的实际合成中。
• Syntheses of a radiolabelled CXCR2 antagonist AZD5069 and its major human metabolite
  作者：Michael J. Hickey、Paul H. Allen、Moya Caffrey、Peter Hansen、Lee P. Kingston、David J. Wilkinson

  DOI：10.1002/jlcr.3429

  日期：2016.9

  The CXCR2 antagonist AZD5069 has been synthesized in tritium and carbon-14-labelled forms. [(3) H]AZD5069 was prepared via reductive dehalogenation of an iodinated precursor with tritium gas to provide material with a specific activity of 25.1 Ci/mmol. [(14) C]AZD5069 was labelled in the pyrimidine ring from [(14) C]thiourea in an overall radiochemical yield of 18%. In addition, a synthetic route to

  CXCR2 拮抗剂 AZD5069 已以氚和碳 14 标记的形式合成。[(3) H] AZD5069 是通过用氚气对碘化前体进行还原脱卤来制备的，以提供比活性为 25.1 Ci/mmol 的材料。[(14) C] AZD5069 被标记在嘧啶环中 [(14) C] 硫脲的总放射化学产率为 18%。此外，还开发了 AZD5069 主要代谢物的合成路线。使用化学选择性 Lindgren-Pinnick 反应从 AZD5069 合成该代谢物，以最大程度地减少硫化物基团的氧化。