4-O-allyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose | 93661-06-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 4-O-allyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose
• 英文别名: (1R,2S,3R,4R,5R)-4-azido-2-prop-2-enoxy-6,8-dioxabicyclo[3.2.1]octan-3-ol
• CAS: 93661-06-4
• 化学式: C₉H₁₃N₃O₄
• 分子量: 227.22
• InChiKey: DGVRDCQNFOXSIT-JGKVKWKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-O-allyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 在 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 Acetic acid (3R,4R,5S,6R)-6-acetoxymethyl-5-allyloxy-3-azido-4-benzyloxy-tetrahydro-pyran-2-yl 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 、 MS 3 Angstroem 、 sodium hydride 、 三丁基氧化锡 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.5h， 生成 4-O-allyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose
  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

• New Synthetic Methods and Reagents for Complex Carbohydrates. VII. Syntheses and Glycosylation Reactions of Glycopyranosyl Dimethylphosphinothioate Series Having a Nonparticipating Group at the C-2 Position
  作者：Takashi Yamanoi、Kazumi Nakamura、Shuji Sada、Masahiro Goto、Yoji Furusawa、Masaaki Takano、Ayumi Fujioka、Kenji Yanagihara、Yuzuru Satoh、Hideaki Hosokawa、Toshiyuki Inazu

  DOI：10.1246/bcsj.66.2617

  日期：1993.9

  nonparticipating group at the C-2 position could be easily prepared by reactions of the corresponding glycopyranose and dimethylphosphinothioyl chloride using butyllithium as a base in tetrahydrofuran. These dimethylphosphinothioates are stable at room temperature and gave the corresponding α-glycosides, predominantly in good yields, by reactions with alcohols using silver perchlorate as an activator in the

  在四氢呋喃中使用丁基锂作为碱，通过相应的吡喃糖和二甲基硫代膦酰氯反应，可以很容易地制备在 C-2 位具有非参与基团的几种吡喃糖基二甲基硫代膦酸酯。这些二甲基硫代膦酸酯在室温下是稳定的，并且在室温下在苯中的分子序列 4A 存在下，通过使用高氯酸银作为活化剂与醇反应，得到相应的 α-糖苷，主要是产率良好。此外，联合使用碘和催化量的高氯酸三苯甲酯作为一种新的活化系统而不是高氯酸银，对于这种糖苷化是有效的。此外，使用本方法制备了H-二糖和Lewis X抗原的合成中间体。
• Kloosterman, M.; Nijs, M. P. de; Boom, J. H. van, Recueil des Travaux Chimiques des Pays-Bas, 1984, vol. 103, # 7-8, p. 243 - 244
  作者：Kloosterman, M.、Nijs, M. P. de、Boom, J. H. van

  DOI：——

  日期：——
• 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.