5-O-benzoyl-3-O-methyl-1,2-O-isopropylidene-α-D-xylofuranose | 58707-34-9

• 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: 5-O-benzoyl-3-O-methyl-1,2-O-isopropylidene-α-D-xylofuranose
• 英文别名: O⁵-benzoyl-O¹,O²-isopropylidene-O³-methyl-α-D-xylofuranose；O⁵-Benzoyl-O¹,O²-isopropyliden-O³-methyl-α-D-xylofuranose；[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate
• CAS: 58707-34-9
• 化学式: C₁₆H₂₀O₆
• 分子量: 308.331
• InChiKey: YRTLYGPRRYJPFB-QVHKTLOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-O-benzoyl-3-O-methyl-1,2-O-isopropylidene-α-D-xylofuranose 在 甲醇 、 barium(II) oxide 作用下， 生成 ((3aR,5R,6S,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-methanol
  参考文献：
  名称：

  Levene; Raymond, Journal of Biological Chemistry, 1933, vol. 102, p. 317,323

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 水 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-O-benzoyl-3-O-methyl-1,2-O-isopropylidene-α-D-xylofuranose
  参考文献：
  名称：

  MODIFIED RNAI AGENTS

  摘要：

  公开号：

  EP2880162B1

文献信息

• Novel <scp>d</scp>-Xylose Derivatives Stimulate Muscle Glucose Uptake by Activating AMP-Activated Protein Kinase α
  作者：Arie Gruzman、Ofer Shamni、Moriya Ben Yakir、Daphna Sandovski、Anna Elgart、Evgenia Alpert、Guy Cohen、Amnon Hoffman、Yehoshua Katzhendler、Erol Cerasi、Shlomo Sasson

  DOI：10.1021/jm8008713

  日期：2008.12.25

  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.
• An Efficient One-Stage Deprotection/Reduction of 1,2-<i>O</i>-Isopropylidene Furanoses to the Corresponding Tetrahydrofurans
  作者：Gregory J. Ewing、Morris J. Robins

  DOI：10.1021/ol9901117

  日期：1999.8.1

  Treatment of 1,2-O-isopropylidenefuranose derivatives with triethylsilane/boron trifluoride etherate results in generation of the corresponding tetrahydrofurans. This one stage process removes the 1,2 O-isopropylidene group with accompanying deoxygenation at the anomeric position and is compatible with several hydroxyl protecting groups.
• Acetolysis: the formation of acyclic by-products
  作者：Karl Bischofberger、Richard H. Hall

  DOI：10.1016/s0008-6215(00)84113-0

  日期：1975.6
• MODIFIED RNAi AGENTS
  申请人：ALNYLAM PHARMACEUTICALS, INC.

  公开号：US20150197746A1

  公开（公告）日：2015-07-16

  One aspect of the present invention relates to double-stranded RNAi (dsRNA) duplex agent capable of inhibiting the expression of a target gene in vivo. The dsRNA duplex comprises one or more xylo modifications in one or both strand. Other aspects of the invention relates to pharmaceutical compositions comprising these dsRNA agents suitable for in vivo therapeutic use, and methods of inhibiting the expression of a target gene by administering these dsRNA agents, e.g., for the treatment of various disease conditions.
• US9708607B2
  申请人：——

  公开号：US9708607B2

  公开（公告）日：2017-07-18