phenyl 2-azido-2-deoxy-4,6-O-benzylidene-1-thio-α-D-mannopyranoside | 402831-58-7

• 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: phenyl 2-azido-2-deoxy-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
• 英文别名: phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-D-mannopyranoside；(2R,4aR,6R,7S,8R,8aS)-7-azido-2-phenyl-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 402831-58-7
• 化学式: C₁₉H₁₉N₃O₄S
• 分子量: 385.444
• InChiKey: HQUROUFKKPKZML-RWLNFDPSSA-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：

  phenyl 2-azido-2-deoxy-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 二苯基亚砜 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 2,4,6-三叔丁基嘧啶 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.42h， 生成 dimethylthexylsilyl 2-azido-2-deoxy-3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1→4)-2-azido-2-deoxy-3-O-acetyl-α-L-fucopyranosyl-(1→3)-2-((2,2,2-trichloroethoxy)-carbonylamino)-2-deoxy-4-O-benzyl-β-D-fucopyranoside
  参考文献：
  名称：

  Synthesis of Staphylococcus aureus Type 5 Trisaccharide Repeating Unit: Solving the Problem of Lactamization

  摘要：

  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.

  DOI：

  10.1021/acs.orglett.5b00031
• 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 、 tetrafluoroboric acid dimethyl ether complex 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 phenyl 2-azido-2-deoxy-4,6-O-benzylidene-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

• 4,6-<i>O</i>-Pyruvyl Ketal Modified<i>N</i>-Acetylmannosamine of the Secondary Cell Wall Polysaccharide of<i>Bacillus anthracis</i>Is the Anchoring Residue for Its Surface Layer Proteins
  作者：Robert N. Chapman、Lin Liu、Geert-Jan Boons

  DOI：10.1021/jacs.8b08857

  日期：2018.12.12

  The secondary cell wall polysaccharide (SCWP) of Bacillus anthracis plays a key role in the organization of the cell envelope of vegetative cells and is intimately involved in host-guest interactions. Genetic studies have indicated that it anchors S-layer and S-layer-associated proteins, which are involved in multiple vital biological functions, to the cell surface of B. anthracis. Phenotypic observations

  炭疽芽孢杆菌的次生细胞壁多糖 (SCWP) 在营养细胞的细胞包膜组织中起关键作用，并与宿主 - 客体相互作用密切相关。遗传研究表明，它将参与多种重要生物学功能的 S 层和 S 层相关蛋白锚定到炭疽芽孢杆菌的细胞表面。表型观察表明 SCWP 末端单元的特定官能团，包括 4,6-O-丙酮酸缩酮和乙酰酯，对于这些蛋白质的结合很重要。这些观察结果是基于遗传操作，并没有得到直接结合研究的证实。为了解决这个问题，开发了一种合成策略，可以提供一系列从 B. 带有碱不稳定乙酰酯和游离氨基的炭疽 SCWP。所得寡糖用于与一组 S 层和 S 层相关蛋白的结合研究，这些蛋白确定了 SCWP 对结合很重要的结构特征。单一的丙酮酸化 ManNAc 单糖与所有蛋白质都表现出强结合，使其成为 S 层蛋白质操作的有前途的结构。SCWP 的乙酰酯和游离胺对结合没有显着影响，这一观察结果与提出的模型相反，在该模型中，SCWP
• Chemoselective glycosylations using sulfonium triflate activator systems
  作者：Jeroen D.C Codée、Leendert J van den Bos、Remy E.J.N Litjens、Herman S Overkleeft、Constant A.A van Boeckel、Jacques H van Boom、Gijs A van der Marel

  DOI：10.1016/j.tet.2003.11.084

  日期：2004.1

  chemoselective glycosylation sequence is described that employs the recently developed BSP/Tf2O and DPS/Tf2O reagent systems to activate thioglycosides. In the first glycosylation event a relatively armed thioglycoside is activated with the BSP/Tf2O activator system and condensed with an acceptor thioglycoside to yield the thiodisaccharide, which is activated with the more potent DPS/Tf2O activator in the

  描述了一种新颖的化学选择性糖基化序列，该序列采用了最近开发的BSP / Tf 2 O和DPS / Tf 2 O试剂系统来激活硫糖苷。在第一次糖基化事件中，相对武装的硫代糖苷被BSP / Tf 2 O活化剂系统激活，并与受体硫糖苷缩合，生成硫二糖，后者在下一次糖基化事件中被更有效的DPS / Tf 2 O活化剂激活。（N-哌啶子基）苯基（S-硫代苯基）硫化物三氟甲磺酸酯的淬灭是在亚磷酸三乙酯活化后形成的，其对于亚磷酸三乙酯的生产至关重要。
• Synthesis of 2-Amino-2-deoxy-β-<scp>d</scp>-mannosides via Stereoselective Anomeric <i>O</i>-Alkylation of 2<i>N</i>,3<i>O</i>-Oxazolidinone-Protected <scp>d</scp>-Mannosamine: Synthesis of the Trisaccharide Repeating Unit of <i>Streptococcus pneumoniae</i> 19F Polysaccharide
  作者：Bishwa Raj Bhetuwal、Fenglang Wu、Padam Prasad Acharya、Prakash Thapa、Jianglong Zhu

  DOI：10.1021/acs.orglett.3c01564

  日期：2023.6.9

  Cesium carbonate-mediated stereoselective anomeric O-alkylation of a 2N,3O-oxazolidinone-protected d-mannosamine with sugar-derived primary or secondary alkyl triflates afforded the corresponding 2-amino-2-deoxy-β-d-mannosides in moderate to good yields and excellent stereoselectivity. The oxazolidinone ring can be opened with aqueous alkali hydroxide to liberate the amine functionality. This method

  碳酸铯介导的 2 N ,3 O-恶唑烷酮保护的d-甘露糖胺与糖衍生的伯或仲烷基三氟甲磺酸酯的立体选择性异头O-烷基化，以中等程度提供相应的 2-氨基-2-脱氧-β- d-甘露糖苷。以获得良好的产率和优异的立体选择性。恶唑烷酮环可以用碱金属氢氧化物水溶液打开以释放胺官能团。该方法已成功应用于肺炎链球菌19F多糖三糖重复单元的合成。
• Ph₂SO/Tf₂O:  a Powerful Promotor System in Chemoselective Glycosylations Using Thioglycosides
  作者：Jeroen D. C. Codée、Remy E. J. N. Litjens、René den Heeten、Herman S. Overkleeft、Jacques H. van Boom、Gijs A. van der Marel

  DOI：10.1021/ol034312t

  日期：2003.5.1

  [GRAPHICS]Diphenylsulfoxide in combination with triflic anhydride provides a very potent thiophilic glycosylation promotor system, capable of activating disarmed thioglycosides. The usefulness of this novel thiophilic activator is illustrated in a successful chemoselective glycosylation sequence in which the donor thioglycoside in the first condensation step may be either armed or disarmed.
• 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.