phenyl 2-O-acetyl-4,6-O-banelidene-1-thio-α-D-mannopyranoside | 340161-12-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-O-acetyl-4,6-O-banelidene-1-thio-α-D-mannopyranoside
• CAS: 340161-12-8
• 化学式: C₂₁H₂₂O₆S
• 分子量: 402.468
• InChiKey: GWTONIWBPILHGT-JRBOJVLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-acetyl-4,6-O-banelidene-1-thio-α-D-mannopyranoside 、 2-O-acetyl-3,4,6-tri-O-benzyl-α,β-D-mannopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以68%的产率得到phenyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthetic yeast oligomannosides as biological probes: α-d-Manp (1→3) α-d-Manp (1→2) α-d-Manp and α-d-Manp (1→3) α-d-Manp (1→2) α-d-Manp (1→2) α-d-Manp as Crohn's disease markers

  摘要：

  The anti-Saccharomyces cerevisiae antibodies (ASCA) are markers for Crohn's disease used for diagnostic, phenotypic characterization and sero-epidermiological studies. Antibody detection is made by different immunoenzymatic tests using S. cerevisiae mannans which are both complex and poorly standardized antigens. Here we construct the major discriminating epitopes comprised within this antigen. When coupled to linker arm and a peptidic carrier to functionalize microtiter plates, they were able to discriminate serological responses between Crohn's disease and ulcerative colitis, another form of inflammatory bowel disease. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.098
• 作为产物：
  描述：

  Α-D-五乙酸甘露糖酯 在 甲醇 、 tetrafluoroboric acid 、 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 sodium 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 phenyl 2-O-acetyl-4,6-O-banelidene-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthetic yeast oligomannosides as biological probes: α-d-Manp (1→3) α-d-Manp (1→2) α-d-Manp and α-d-Manp (1→3) α-d-Manp (1→2) α-d-Manp (1→2) α-d-Manp as Crohn's disease markers

  摘要：

  The anti-Saccharomyces cerevisiae antibodies (ASCA) are markers for Crohn's disease used for diagnostic, phenotypic characterization and sero-epidermiological studies. Antibody detection is made by different immunoenzymatic tests using S. cerevisiae mannans which are both complex and poorly standardized antigens. Here we construct the major discriminating epitopes comprised within this antigen. When coupled to linker arm and a peptidic carrier to functionalize microtiter plates, they were able to discriminate serological responses between Crohn's disease and ulcerative colitis, another form of inflammatory bowel disease. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.098

文献信息

• Efficient routes toward the synthesis of the D-<i>rhamno</i>-trisaccharide related to the A-band polysaccharide of <i>Pseudomonas aeruginosa</i>
  作者：Aritra Chaudhury、Sajal K Maity、Rina Ghosh

  DOI：10.3762/bjoc.10.153

  日期：——

  pyranoside by radical-mediated redox rearrangement in high yields and regioselectivity. The D-rhamno-thioglycosides so obtained allowed efficient access to the trisaccharide target via stepwise glycosylation as well as a one-pot glycosylation protocol. In a different approach, a 4,6-O-benzylidene D-manno-trisaccharide derivative was synthesized, which upon global 6-O-deoxygenation followed by deprotection

  目前的工作描述了合成三糖重复单元 [α-D-Rhap-(1-->3)-α-D-Rhap-(1-->3)-α-D-Rhap] 的有效途径与铜绿假单胞菌的 A 带多糖。关键步骤之一涉及通过自由基介导的氧化还原重排以高产率和区域选择性对部分或完全酰化的 4,6-O-benzylidene-1-thiomannopyranoside 进行 6-O-脱氧。如此获得的 D-鼠李糖苷允许通过逐步糖基化以及一锅糖基化方案有效地获得三糖目标。在不同的方法中，合成了 4,6-O-亚苄基 D-甘露糖三糖衍生物，其在全局 6-O-脱氧和脱保护后生成目标 D-鼠李糖三糖。