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 | 340161-13-9

• 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-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
• CAS: 340161-13-9
• 化学式: C₅₀H₅₂O₁₂S
• 分子量: 877.022
• InChiKey: RLPKVZIYPIJHOC-RKGILCGBSA-N

物化性质

• 熔点：
  58-59 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  899.8±65.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.98
• 重原子数：
  63.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  126.44
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  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 在 吡啶 、 丙烷-1-硫醇 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 phenyl (2-O-acetyl-3,4,6,-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-acetyl-1-thio-α-D-mannopyranoside)
  参考文献：
  名称：

  Experimental observations on the regioselectivity of glycosylation of a 4,6-diol system in the β-d-mannopyranosyl unit of a N-glycan pentasaccharide core structure

  摘要：

  The regioselectivity of glycosylation of a 4,6-diol system in the p-mannopyranosyl unit of a N-glycan pentasaccharide core structure is found to be strongly dependent on the structure of the glycosyl donor. While glycosylation with a 2-O-acetyl-D-mannopyranosyl trichloroacetimidate and with a D-mannopyranosyl (alpha 1 -> 3) 2-O-acetyl mannopyranosyl trichoroacetimidate regioselectively occurs at the primary OH-6 position, reaction with D-mannopyranosyl (alpha 1 -> 6) mannopyranosyl 2-O-benzoyl, 2-O-acetyl and 2-O-pivaloyl trichloroacetimidate results in approximately 1:1 mixture of regioisomers at primary OH-6 and secondary OH-4 positions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.05.006
• 作为产物：
  描述：

  苯基1-硫代吡喃己糖苷 在 tetrafluoroboric acid 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 camphor-10-sulfonic acid 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 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