(1R,2S,3R,4R,5R)-4-azido-3-phenylmethoxy-2-prop-2-enoxy-6,8-dioxabicyclo[3.2.1]octane | 105265-70-1

• 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: (1R,2S,3R,4R,5R)-4-azido-3-phenylmethoxy-2-prop-2-enoxy-6,8-dioxabicyclo[3.2.1]octane
• CAS: 105265-70-1
• 化学式: C₁₆H₁₉N₃O₄
• 分子量: 317.345
• InChiKey: RAZINGMFEJRTRV-OXGONZEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R,4R,5R)-4-azido-3-phenylmethoxy-2-prop-2-enoxy-6,8-dioxabicyclo[3.2.1]octane 在 哌啶 、 叔丁基二甲硅基三氟甲磺酸酯 、 caesium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 (2R,3S,4S,5R,6R)-5-Acetoxy-3-((2R,3R,4R,5S,6R)-6-acetoxymethyl-5-allyloxy-3-azido-4-benzyloxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and biological activity of oligomer-model compounds containing units of a key platelet-binding disaccharide of heparin

  摘要：

  A key disaccharide unit in heparin, O-(2-deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranosyl)-(1-->4)-2-O-sulfo-alpha-L-idopyranosyluronic acid, was previously found to be responsible for the binding interaction of heparin to platelets. A clustering effect to enhance the binding was found to be dependent on the number and frequency of the disaccharide units in a heparin molecule. To systematically examine the clustering effect, three oligomer-model compounds containing two or three units of the disaccharide were synthesized. These compounds inhibited (3)H-Iabelled heparin binding to human platelets more strongly than a compound containing only one unit of the disaccharide, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01084-9
• 作为产物：
  描述：

  D-葡萄烯糖 在 sodium azide 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (1R,2S,3R,4R,5R)-4-azido-3-phenylmethoxy-2-prop-2-enoxy-6,8-dioxabicyclo[3.2.1]octane
  参考文献：
  名称：

  简便地合成麦角环氧化物和2-叠氮基-2-脱氧-β-d-吡喃葡萄糖的选择性封闭衍生物

  摘要：

  由一锅中的d-葡萄糖制备1,6：2,3-Dianhydro-β-d-吡喃葡萄糖及其3-烷基化衍生物，总分离产率为60-70％，并将这些Cerny环氧化物进一步方便地转化为选择性通过环的叠氮基开环来封闭2-叠氮基-2-脱氧-β-d-吡喃葡萄糖衍生物。

  DOI：

  10.1016/s0040-4039(01)01354-5

文献信息

• Convergent synthesis of an inner core GPI of sperm CD52
  作者：Jie Xue、Zhongwu Guo

  DOI：10.1016/s0960-894x(02)00301-3

  日期：2002.8

  An inner core of the GPI anchor of sperm CD52 antigens was synthesized by a highly convergent process using specially modified inositol, glucosamine and phospholipid as key building blocks. This paper also presents a new and efficient procedure to prepare 1,2,6-differentiated derivatives of inositol for GPI syntheses. (C) 2002 Elsevier Science Ltd. All rights reserved.
• A facile synthesis of Cerny epoxides and selectively blocked derivatives of 2-azido-2-deoxy-β-d-glucopyranose
  作者：Jie Xue、Zhongwu Guo

  DOI：10.1016/s0040-4039(01)01354-5

  日期：2001.9

  1,6:2,3-Dianhydro-β-d-glucopyranose and its 3-alkylated derivatives were prepared from d-glucal in one pot with overall isolated yields of 60–70%, and these Cerny epoxides were further conveniently converted to selectively blocked 2-azido-2-deoxy-β-d-glucopyranose derivatives by azido opening of the epoxide ring.

  由一锅中的d-葡萄糖制备1,6：2,3-Dianhydro-β-d-吡喃葡萄糖及其3-烷基化衍生物，总分离产率为60-70％，并将这些Cerny环氧化物进一步方便地转化为选择性通过环的叠氮基开环来封闭2-叠氮基-2-脱氧-β-d-吡喃葡萄糖衍生物。
• Synthesis and biological activity of oligomer-model compounds containing units of a key platelet-binding disaccharide of heparin
  作者：Shuhei Koshida、Yasuo Suda、Yasuhiro Fukui、Julie Ormsby、Michael Sobel、Shoichi Kusumoto

  DOI：10.1016/s0040-4039(99)01084-9

  日期：1999.7

  A key disaccharide unit in heparin, O-(2-deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranosyl)-(1-->4)-2-O-sulfo-alpha-L-idopyranosyluronic acid, was previously found to be responsible for the binding interaction of heparin to platelets. A clustering effect to enhance the binding was found to be dependent on the number and frequency of the disaccharide units in a heparin molecule. To systematically examine the clustering effect, three oligomer-model compounds containing two or three units of the disaccharide were synthesized. These compounds inhibited (3)H-Iabelled heparin binding to human platelets more strongly than a compound containing only one unit of the disaccharide, (C) 1999 Elsevier Science Ltd. All rights reserved.