O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-D-galactopyranosyl fluoride | 146453-40-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-D-galactopyranosyl fluoride
• 英文别名: (3R,4S,5S,6R)-2-fluoro-3,4,5-tris(phenylmethoxy)-6-[[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxymethyl]oxane
• CAS: 146453-40-9
• 化学式: C₆₁H₆₃FO₁₀
• 分子量: 975.164
• InChiKey: GIBQKJTXPZWDMS-IQIWPMODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.15
• 重原子数：
  72.0
• 可旋转键数：
  25.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  92.3
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-D-galactopyranosyl fluoride 、 (2S,3S,4R)-2-hexacosylamino-3,4-di-O-benzyl-1,3,4-octadecanetriol 在 silver perchlorate 、 tin(ll) chloride 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Immunostimulatory activities of monoglycosylated α-d-pyranosylceramides

  摘要：

  We compared the immunostimulatory effects of chemically synthesized alpha-galactosylceramides (alpha-GalCers), alpha-glucosylceramides (alpha-GluCers), 6 "-monoglycosylated alpha-GalCer and 6 "- or 4 "-monoglycosylated alpha-GluCer and made the following observations: (1) the length of the fatty acid side chain in the ceramide portions greatly affects the immunostimulatory effects of alpha-GalCers and alpha-GluCers; (2) the configuration of the 4 "-hydroxyl group of the inner pyranose moiety plays an important role in the immunostimulatory effects of monoglycosylated alpha-D-pyranosylceramides; (3) the free 4 "-hydroxyl group of the inner pyranose of monoglycosylated alpha-D-pyranosylceramides plays a more important role in their immunostimulatory effects than the free 6 "-hydroxyl group. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00169-7
• 作为产物：
  描述：

  甲基2,3,4,6-四-O-苄基-1-硫代吡喃己糖苷 在 ammonium cerium(IV) nitrate 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 生成 O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-D-galactopyranosyl fluoride
  参考文献：
  名称：

  Synthetic study on glycophosphatidyl inositol (GPI) anchor of trypanosoma brucei: Glycoheptaosyl core

  摘要：

  DOI：

  10.1016/s0040-4039(00)97383-0

文献信息

• Stereoselective total synthesis of the glycosyl phosphatidylinositol (GPI) anchor of Trypanosoma brucei
  作者：Chikara Murakata、Tomoya Ogawa

  DOI：10.1016/0008-6215(92)80081-b

  日期：1992.11

  The total synthesis of O-(O-[6-O-(2-aminoethylphosphono)-alpha-D-mannopyranosyl]-(1-->2)- O-alpha- D-mannopyranosyl-(1-->6)-O-[O-alpha-D-galactopyranosyl-(1-->6)-alpha-D- galactopyranosyl-(1-->3)]-O-alpha-D-mannopyranosyl-(1-->4)-2-amino-2-deo xy- alpha-D-glucopyranosyl)-(1-->6)-[1-O-(1,2-dimyristoyl-sn-glycero-3-phosp hono) - 1D-myo-inositol], the GPI anchor of Trypanosoma brucei was achieved for

  O-（O- [6-O-（2-氨基乙基膦酰基）-α-D-甘露吡喃糖基]-（1-> 2）-O-α-D-甘露吡喃糖基-（1-> 6）的全合成-O- [O-α-D-半乳糖吡喃糖基-（1-> 6）-α-D-半乳糖吡喃糖基-（1-> 3）]-O-α-D-甘露吡喃糖基-（1-> 4） -2-氨基-2-deo xy-α-D-吡喃葡萄糖基）-（1-> 6）-[1-O-（1,2-二肉豆蔻酰基-sn-甘油-3-磷孢子）-1D-肌-肌醇]，首次获得了布鲁氏锥虫的GPI锚点。GPI分子的核心结构，即糖庚糖基部分，是由O- [O-（2,4-di-O-苄基-α-D-甘露吡喃糖基-（1-> 4）- 2-叠氮基3,6-二-O-苄基-2-脱氧-D-吡喃葡萄糖基]-（1-> 6）-2,3,4,5-四-O-苄基-1-O- （4-甲氧基苄基）-D-肌醇，O-（2,3,4,6-四-O-苄基-α-D-吡喃半乳糖基）-（1-> 6）-2
• MURAKATA, CHIKARA;OGAWA, TOMOYA, TETRAHEDRON LETT., 31,(1990) N7, C. 2439-2442
  作者：MURAKATA, CHIKARA、OGAWA, TOMOYA

  DOI：——

  日期：——