5-O-trityl-3-O-butyl-1,2-isopropylidene-α-D-xylopyranoside | 892499-34-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5-O-trityl-3-O-butyl-1,2-isopropylidene-α-D-xylopyranoside
• 英文别名: 1,2-O-isopropylidene-3-butoxy-5-O-acetyl-D-xylofuranose；(3aR,5R,6S,6aR)-6-butoxy-2,2-dimethyl-5-(trityloxymethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 892499-34-2
• 化学式: C₃₁H₃₆O₅
• 分子量: 488.624
• InChiKey: MNXAYPBBWWSMMX-VJLHXPKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-O-trityl-3-O-butyl-1,2-isopropylidene-α-D-xylopyranoside 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 以34.6%的产率得到3-O-butyl-1,2-isopropylidene-α-D-xylopyranoside
  参考文献：
  名称：

  Novel d-Xylose Derivatives Stimulate Muscle Glucose Uptake by Activating AMP-Activated Protein Kinase α

  摘要：

  Type 2 diabetes mellitus has reached epidemic proportions; therefore, the search for novel antihyperglycemic drugs is intense. We have discovered that D-Xylose increases the rate of glucose transport in a non-insulin-dependent manner in rat and human myotubes in vitro. Due to the unfavorable pharmacokinetic properties Of D-Xylose we aimed at synthesizing active derivatives with improved parameters. Quantitative structure-activity relationship analysis identified critical hydroxyl groups in D-xylose. These data were used to synthesize various hydrophobic derivatives Of D-Xylose of which compound 19 the was most potent compound in stimulating the rate of hexose transport by increasing the abundance of glucose transporter-4 in the plasma membrane of myotubes. This effect resulted from the activation of AMP-activated protein kinase without recruiting the insulin transduction mechanism. These results show that lipophilic D-Xylose derivatives may serve as prototype molecules for the development of novel anti hyperglycemic drugs for the treatment of diabetes.

  DOI：

  10.1021/jm8008713
• 作为产物：
  描述：

  1-碘丁烷 、 1,2-O-(异丙亚基)-5-O-(三苯基甲基)-alpha-D-呋喃木糖 在 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以41%的产率得到5-O-trityl-3-O-butyl-1,2-isopropylidene-α-D-xylopyranoside
  参考文献：
  名称：

  WO2006/66080

  摘要：

  公开号：

文献信息

• 3,5-DISUBSTITUTED AND 3,5,7-TRISUBSTITUTED-3H-OXAZOLO AND 3H-THIAZOLO[4,5-d]PYRIMIDIN-2-ONE COMPOUNDS AND PRODRUGS THEREOF
  申请人：Webber Stephen E.

  公开号：US20110275589A1

  公开（公告）日：2011-11-10

  The invention is directed to 3,5-disubstituted and 3,5,7-trisubstituted-3H-oxazolo and 3H-thiazolo[4,5-d]pyrimidin-2-one compounds and prodrugs thereof that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and pharmaceutical compositions containing them, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds and prodrugs.

  本发明涉及具有免疫调节活性的3,5-二取代和3,5,7-三取代-3H-噁唑并[4,5-d]嘧啶-2-酮化合物及其前药。本发明还涉及使用此类化合物及其前药的治疗或预防用途，以及含有它们的制药组合物和通过给予这些化合物和前药的有效量来治疗本文所述疾病和疾病的方法。
• 3,5-DISUBSTITUTED AND 3,5,7-TRISUBSTITUTED-3H-OXAZOLO AND 3H-THIAZOLO[4,5-D]PYRIMIDIN-2-ONE COMPOUNDS AND PRODRUGS THEREOF
  申请人：Webber Stephen E.

  公开号：US20120121541A1

  公开（公告）日：2012-05-17

  The invention is directed to 3,5-disubstituted and 3,5,7-trisubstituted-3H-oxazolo and 3H-thiazolo[4,5-d]pyrimidin-2-one compounds and prodrugs thereof that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and pharmaceutical compositions containing them, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds and prodrugs.

  本发明涉及具有免疫调节活性的3,5-二取代和3,5,7-三取代-3H-噁唑和3H-噻唑[4,5-d]嘧啶-2-酮化合物及其前药。本发明还涉及使用这些化合物和前药的治疗或预防用途，以及含有它们的制药组合物，并通过给予这些化合物和前药的有效剂量来治疗本文所述的疾病和障碍的方法。
• 3,5-Disubstituted and 3,5,7-Trisubstituted-3H-Oxazolo and 3H-Thiazolo[4,5-d]pyrimidin-2-one Compounds and Prodrugs Thereof
  申请人：Webber Stephen E.

  公开号：US20130259831A1

  公开（公告）日：2013-10-03

  The invention is directed to 3,5-disubstituted and 3,5,7-trisubstituted-3H-oxazolo and 3H-thiazolo[4,5-d]pyrimidin-2-one compounds and prodrugs thereof that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and pharmaceutical compositions containing them, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds and prodrugs.

  该发明涉及具有免疫调节活性的3,5-二取代和3,5,7-三取代-3H-噁唑并[4,5-d]嘧啶-2-酮化合物及其前药。该发明还涉及使用这些化合物的治疗或预防用途，以及含有它们的制药组合物，以及通过给予这些化合物和前药的有效量来治疗本文所述的疾病和障碍的方法。
• 3, 5-disubstituted and 3,5,7-trisubstituted-3H-oxazolo [4,5-d]pyrimidin-2-one compounds and prodrugs thereof
  申请人：Anadys Pharmaceuticals, Inc.

  公开号：EP2561872A1

  公开（公告）日：2013-02-27

  The present application concerns a compound selected from or a pharmaceutically acceptable salt thereof. The applications also concerns pharmaceutical uses of the compound or a pharmaceutically acceptable salt thereof

  本申请涉及一种选自或其药学上可接受的盐的化合物。 本申请还涉及该化合物或其药学上可接受的盐的药物用途
• WO2006/66080
  申请人：——

  公开号：——

  公开（公告）日：——