1,6-anhydro-2-azido-2-deoxy-4-O-(tert-butyldimethylsilyl)-β-D-glucopyranose | 88261-51-2

• 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: 1,6-anhydro-2-azido-2-deoxy-4-O-(tert-butyldimethylsilyl)-β-D-glucopyranose
• 英文别名: 1,6-anhydro-2-azido-4-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose；1,6-anhydro-2-azide-4-O-(tert-buthyldimethylsilyl)-2-deoxy-β-D-glucopyranose；(1R,2S,3R,4R,5R)-4-azido-2-[tert-butyl(dimethyl)silyl]oxy-6,8-dioxabicyclo[3.2.1]octan-3-ol
• CAS: 88261-51-2
• 化学式: C₁₂H₂₃N₃O₄Si
• 分子量: 301.418
• InChiKey: LIPXIJOALNMOLF-ISUQUUIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  96.68
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-2-azido-2-deoxy-4-O-(tert-butyldimethylsilyl)-β-D-glucopyranose 在 吡啶 、 三氟化硼乙醚 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 21.5h， 生成
  参考文献：
  名称：

  Synthesis of 5-Thio-l-fucose-Containing Disaccharides, as Sequence-Specific Inhibitors, and 2‘-Fucosyllactose, as a Substrate of α-l-Fucosidases

  摘要：

  Four 5-thio-L-fucose-containing disaccharides having alpha(1-->6), alpha(1-->3), alpha(1-->4)GlcNAc, and alpha(1-->2-Gal linkages (compounds 1-4, respectively) were synthesized as potential alpha-L-fucosidase inhibitors. The glycosylation reactions using 2,3,4-tri-O-acetyl-5-thio-L-fucopyranosyl trichloroacetimidate as a glycosyl donor and BF3 . OEt(2) as a catalyst gave mainly alpha-linked disaccharides. Only alpha(1-->2)-linked disaccharide 4 showed inhibitory activity (K-i = 0.21 mM) against Bacillus alpha-L-fucosidase which hydrolyzes the Fuc alpha(1-->2) linkage specifically. The results suggested that sequence specificity of an enzyme could be estimated from the inhibitory activities of the compounds 1-4. In contrast, every disaccharide showed inhibitory activity (K-i = 30-91 mu M) against bovine epididymis alpha-L-fucosidase.

  DOI：

  10.1021/jo961725h
• 作为产物：
  描述：

  a-无水葡萄糖酯 在 硫酸 、 溶剂黄146 咪唑 、 氢溴酸 、 sodium methylate 、 碳酸氢钠 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 1,6-anhydro-2-azido-2-deoxy-4-O-(tert-butyldimethylsilyl)-β-D-glucopyranose
  参考文献：
  名称：

  PROCESS FOR PREPARING HEPARINOIDS AND INTERMEDIATES USEFUL IN THE SYNTHESIS THEREOF

  摘要：

  公开了合成因子Xa抗凝剂磺达肝癸钠及其相关化合物的方法。提供了受保护的五糖中间体以及通过一系列去保护和磺化反应将受保护五糖中间体转化为磺达肝癸钠的工业规模生产的高效和可扩展过程。

  公开号：

  US20130005954A1

文献信息

• Total Synthesis of Anticoagulant Pentasaccharide Fondaparinux
  作者：Tiehai Li、Hui Ye、Xuefeng Cao、Jiajia Wang、Yonghui Liu、Lifei Zhou、Qiang Liu、Wenjun Wang、Jie Shen、Wei Zhao、Peng Wang

  DOI：10.1002/cmdc.201400019

  日期：2014.5

  The anticoagulant pentasaccharide fondaparinux was synthesized using an improved and optimized synthetic strategy including a convergent [3+2] coupling approach, orthogonal protecting groups and various glycosyl donors. The new methods of glycosylation were also used for controlling the stereochemical configuration and improving the yield of the glycosylation. In addition, HPLC and NMR methods to monitor

  抗凝五糖磺达肝素是使用改进和优化的合成策略合成的，包括收敛的[3 + 2]偶联方法，正交保护基和各种糖基供体。糖基化的新方法也用于控制立体化学构型和提高糖基化的产率。另外，采用HPLC和NMR方法监测磺达肝素的全合成过程。这项工作在相关文献的基础上为磺达肝素的合成和分析提供了详尽的阐述，并为肝素样低聚糖的合成提供了丰富的信息。
• Synthesis of 5-thio-l-fucose-containing blood group antigens H-type 2 and Lewis X (Lex)
  作者：Masayuki Izumi、Osamu Tsuruta、Hironobu Hashimoto、Shin Yazawa

  DOI：10.1016/0040-4039(96)00124-4

  日期：1996.3

  Two blood group antigens, H-type 2 and Lewis X trisaccharides containing 5-thio-l-fucose instead of l-fucose, were synthesized. 2-Azido-2-deoxy-lactose derivative 11 was used as the common disaccharide intermediate. 5-Thio-l-fucosylation of the 2′-OH and 3-OH groups of 1,6-anhydro-2-azido-2-deoxy-lactose derivative by a trichloroacetimidate method gave α-linked trisaccharides stereoselectively.

  合成了两种血型抗原，分别是H型2和Lewis X三糖，它们含有5-硫基-1-岩藻糖而不是1-岩藻糖。使用2-叠氮基-2-脱氧乳糖衍生物11作为常见的二糖中间体。通过三氯乙亚氨酸酯方法对1，6-脱水-2-叠氮基-2-脱氧乳糖的衍生物的2'-OH和3-OH基团的5-硫-1-岩藻糖基化立体选择性地得到α-连接的三糖。
• The Oxolane Ring Opening of Some Muramic Acid Derivatives Under Acidic Conditions
  作者：Justyna Samaszko-Fiertek、Barbara Dmochowska、Rafał Slusarz、Janusz Madaj

  DOI：10.2174/1570178615666180119152605

  日期：2018.7.2

  process led to the preparation of compounds with very good yields (80%, even 98%). In the first attempt the mixture of TFA/Ac2O (1:9) was used. Besides the main product 4, the 3,4-di-Oacetyl- 1,6-anhydro-2-azide-2-deoxy-β-D-glucopyranose was observed as a side product. Main product 4 was obtained as the mixture of α and β (2:1) anomers. Better stereoselectivity was obtained using Sc(OTf)3. In this case

  1，6-脱水糖的合成在文献中是众所周知的。二氧戊环具有至少两种类型的性质。可用作保护基和反应位点。这项工作讨论了山酰胺酸衍生物的1，6-脱水环的裂解。为了在1，6-脱水-D-葡萄糖衍生物中诱导二氧戊环开环，使用了三种类型的试剂（TFA / Ac2O，Sc（OTf）3 / Ac2O，H2SO4 / Ac2O）。该方法通常在糖化学中用于打开1,6-脱水环。该过程导致以非常高的收率（80％，甚至98％）制备化合物。 在第一次尝试中，使用了TFA / Ac2O（1：9）的混合物。除了副产物4以外，还观察到副产物3，4-二-O-乙酰基-1，6-脱水-2-叠氮基-2-脱氧-β-D-吡喃葡萄糖。获得主要产物4，为α和β（2：1）异构体的混合物。使用Sc（OTf）3可获得更好的立体选择性。在这种情况下，收到的主产品具有β配置。使用H2SO4和Ac2O的混合物可获得最佳收率（65％），并且分离了N-乙酰基1
• α:β Selectivity in the synthesis of 3-substituted, 4-methyl umbelliferone glycosides of N-acetyl glucosamine and chitobiose
  作者：Anjali R.S. Ganguli、James K. Coward

  DOI：10.1016/j.tetasy.2004.11.053

  日期：2005.1

  The influence of phenolic acceptor nucleophilicity; for example, 3-substituted, 4-methylumbelliferones, and glycosyl donor electrophilicity; for example, 3- and 4-substituted N-acetylglucosamines, on glycosylation stereochemistry has been evaluated. In a systematic comparison, the stereochemical outcome as well as the reaction yield appeared to be influenced by the 3- and 4-substituents of the donor as well as the 3-substituent of the aryl acceptor. In the context of synthesizing a fluorogenic substrate for oligosaccharyltransferase, an alpha-glycoside was desired. Although most acceptor-donor pairs led to predominantly or exclusively the beta-glycoside, reaction of the most activated (3,4-di-O-benzyl) donor and the least nucleophilic acceptor (3-Br), resulted in a 1:1 ratio of alpha,beta arylglycosides. (C) 2004 Elsevier Ltd. All rights reserved.
• Boeckel, C. A. A. van; Aelst, S. F. van; Beetz, T., Recueil des Travaux Chimiques des Pays-Bas, 1983, vol. 102, # 9, p. 415 - 416
  作者：Boeckel, C. A. A. van、Aelst, S. F. van、Beetz, T.

  DOI：——

  日期：——