phenyl 2-azido-2-deoxy-1-thio-α-D-mannopyranoside | 166516-71-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-azido-2-deoxy-1-thio-α-D-mannopyranoside
• 英文别名: Phenyl 2-azido-2-deoxy-1-thio-I+/--D-mannopyranoside；(2R,3S,4R,5S,6R)-5-azido-2-(hydroxymethyl)-6-phenylsulfanyloxane-3,4-diol
• CAS: 166516-71-8
• 化学式: C₁₂H₁₅N₃O₄S
• 分子量: 297.335
• InChiKey: VDPWHERVMHFLNT-IYKVGLELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 2-azido-2-deoxy-1-thio-α-D-mannopyranoside 在 吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碘苯二乙酸 、 sodium hydride 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 9.0h， 生成 methyl (phenyl 4-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosid)uronate
  参考文献：
  名称：

  1-硫甘露糖叠氮基吡喃糖苷和1-硫甘露糖叠氮醛酸酯的糖苷化特性研究

  摘要：

  研究了具有多种吸电子取代基的 1-硫代甘露糖肼与 Ph2SO/Tf2O 和 NIS/TMSOTf 试剂系统的糖基化特性。此外，还讨论了完全保护的三糖 26 的组装，该三糖对应于肠细菌共同抗原的重复单元，使用正交和化学选择性偶联策略并基于我们的糖基化研究结果进行了讨论。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  DOI：

  10.1002/ejoc.200600759
• 作为产物：
  描述：

  2-azido-2-deoxy-D-mannopyranose 在 4-二甲氨基吡啶 吡啶 、 三氟化硼乙醚 、 potassium tert-butylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 phenyl 2-azido-2-deoxy-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  A novel approach towards the stereoselective synthesis of 2-azido-2-deoxy-β-d-mannosides

  摘要：

  Low temperature mannosylation of glycosyl acceptors under the agency of S-(4-methoxyphenyl) benzenethiosulfinate (MPBT) and trifluoromethanesulfonic anhydride (Tf2O) with p-methoxyphenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-alpha -D-mannopyranoside, readily available from D-mannosamine hydrochloride, affords 2-azido-2-deoxy-D-mannosides with high beta -selectivity in good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01880-9

文献信息

• Facile preparation of glycosyl donors for oligosaccharide synthesis: 2-azido-2-deoxyhexopyranosyl building blocks
  作者：Therese Buskas、Per J. Garegg、Peter Konradsson、Jean-Luc Maloisel

  DOI：10.1016/s0957-4166(00)86294-1

  日期：1994.11

  Facile routes to the 2-azido-2-deoxy-1-thioglycosides 6, 7, 15, and 18 and of the 2-azido-2-deoxy-4-pentenoglycoside 11, are described. These are useful intermediates for the synthesis of oligo-saccharides containing alpha-D-2-amino-2-deoxy (or 2-acetamido-2-deoxy) hexosyl residues in the galacto-, gluco-, and manno- series.
• Synthesis of <i>Staphylococcus aureus</i> Type 5 Trisaccharide Repeating Unit: Solving the Problem of Lactamization
  作者：Ivan A. Gagarinov、Tao Fang、Lin Liu、Apoorva D. Srivastava、Geert-Jan Boons

  DOI：10.1021/acs.orglett.5b00031

  日期：2015.2.20

  The chemical synthesis of an orthogonally protected trisaccharide derived from the polysaccharide of Staphylococcus aureus Type 5, which is an attractive candidate for the development of immunotherapies, is described. The challenging alpha-fucosylation and beta-mannosylation are addressed through the careful choice of protecting groups. Lactamization of a beta-D-ManpNAcA moiety during deprotection was avoided by a late stage oxidation approach. Versatility of the trisaccharide was demonstrated by its transformation into a spacer-containing repeating unit suitable for immunological investigations.
• A novel approach towards the stereoselective synthesis of 2-azido-2-deoxy-β-d-mannosides
  作者：Remy E.J.N Litjens、Michiel A Leeuwenburgh、Gijsbert A van der Marel、Jacques H van Boom

  DOI：10.1016/s0040-4039(01)01880-9

  日期：2001.12

  Low temperature mannosylation of glycosyl acceptors under the agency of S-(4-methoxyphenyl) benzenethiosulfinate (MPBT) and trifluoromethanesulfonic anhydride (Tf2O) with p-methoxyphenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-alpha -D-mannopyranoside, readily available from D-mannosamine hydrochloride, affords 2-azido-2-deoxy-D-mannosides with high beta -selectivity in good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Study of the Glycosidation Properties of 1-Thiomannosazidopyranosides and 1-Thiomannosaziduronic Acid Esters
  作者：Leendert J. van den Bos、Boudewijn A. Duivenvoorden、Martijn C. de Koning、Dmitri V. Filippov、Herman S. Overkleeft、Gijsbert A. van der Marel

  DOI：10.1002/ejoc.200600759

  日期：2007.1

  A study of the glycosylation properties of 1-thiomannosazides with a variety of electron-withdrawing substituents in combination with the Ph2SO/Tf2O and NIS/TMSOTf reagent systems is presented. Further, assembly of the fully protected trisaccharide 26, which corresponds to the repeating unit of the enterobacterial common antigen, using both an orthogonal and a chemoselective coupling strategy and based

  研究了具有多种吸电子取代基的 1-硫代甘露糖肼与 Ph2SO/Tf2O 和 NIS/TMSOTf 试剂系统的糖基化特性。此外，还讨论了完全保护的三糖 26 的组装，该三糖对应于肠细菌共同抗原的重复单元，使用正交和化学选择性偶联策略并基于我们的糖基化研究结果进行了讨论。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)