2-azido-4,6-O-benzylidene-2-deoxy-1-thio-D-glucopyranoside | 310870-34-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-D-glucopyranoside
• 英文别名: (2R,4aR,7R,8R,8aS)-7-azido-2-phenyl-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 310870-34-9
• 化学式: C₁₉H₁₉N₃O₄S
• 分子量: 385.444
• InChiKey: HQUROUFKKPKZML-NXWNTDFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  87.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-azido-4,6-O-benzylidene-2-deoxy-1-thio-D-glucopyranoside 在 吡啶 、 sodium azide 、 四丁基硫酸氢铵 、 sodium hydride 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(2R,3R,4R,5R)-5-azido-2-(azidomethyl)-4-phenylmethoxy-6-phenylsulfanyloxan-3-yl] acetate
  参考文献：
  名称：

  Synthesis of aminoglycoside derivatives on a Cbz-type heavy fluorous tag

  摘要：

  Four aminoglycoside derivatives containing a 2,6-diamino-2,6-dideoxy-D-glucopyranose disaccharide structure were successfully prepared by using a Cbz-type heavy fluorous tag in a fluorous synthesis. A Cbz-type heavy fluorous tag was prepared using the hexakis(fluorous chain)-type alcohol 11, and the fluorous alcohol 11 was recovered in good yield after the synthesis of aminoglycoside derivatives. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.064
• 作为产物：
  描述：

  phenyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-α/β-D-glucopyranoside 在 sodium methylate 、 (+)-10-camphorsulfonic acid 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of aminoglycoside derivatives on a Cbz-type heavy fluorous tag

  摘要：

  Four aminoglycoside derivatives containing a 2,6-diamino-2,6-dideoxy-D-glucopyranose disaccharide structure were successfully prepared by using a Cbz-type heavy fluorous tag in a fluorous synthesis. A Cbz-type heavy fluorous tag was prepared using the hexakis(fluorous chain)-type alcohol 11, and the fluorous alcohol 11 was recovered in good yield after the synthesis of aminoglycoside derivatives. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.064

文献信息

• Inositolphosphoglycan Mediators Structurally Related to Glycosyl Phosphatidylinositol Anchors: Synthesis, Structure and Biological Activity
  作者：Manuel Martín-Lomas、Noureddine Khiar、Salud García、Jean-Luc Koessler、Pedro M. Nieto、Thomas W. Rademacher

  DOI：10.1002/1521-3765(20001002)6:19<3608::aid-chem3608>3.0.co;2-q

  日期：2000.10.2

  The preparation of the pseudopentasaccharide 1a, an inositolphosphoglycan (IPG) that contains the conserved linear structure of glycosyl phosphatidylinositol anchors (GPI anchors), was carried out by using a highly convergent 2+3-block synthesis approach which involves imidate and sulfoxide glycosylation reactions. The preferred solution conformation of this structure was determined by using NMR spectroscopy and molecular dynamics simulations prior to carrying out quantitative structure-activity relationship studies in connection with the insulin signalling process. The ability of 1a to stimulate lipogenesis in rat adipocites as well as to inhibit cAMP dependent protein kinase and to activate pyruvate dehydrogenase phosphatase was investigated. Compound 1a did not show any significant activity, which may be taken as a strong indication that the GPI anchors are not the precursors of the IPG mediators.
• 10.1002/(sici)1099-0690(200004)2000:8<1547::aid-ejoc1547<3.0.co;2-c
  作者：Martin-Lomas, Manuel、Flores-Mosquera, Maria、Chiara, Jose Luis

  DOI：10.1002/(sici)1099-0690(200004)2000:8<1547::aid-ejoc1547<3.0.co;2-c

  日期：——