2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside | 250123-39-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Man(a1-4)[Bz(-2)][Bz(-3)]Gal(b1-6)[Bz(-2)][Bz(-3)][Bz(-4)]Gal(b)-O-EtTMS；[(2R,3R,4S,5S,6R)-3,4,5-tribenzoyloxy-6-[(2R,3S,4S,5R,6R)-4,5-dibenzoyloxy-2-(hydroxymethyl)-6-[[(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(2-trimethylsilylethoxy)oxan-2-yl]methoxy]oxan-3-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 250123-39-8
• 化学式: C₈₆H₈₀O₂₅Si
• 分子量: 1541.65
• InChiKey: KPLCYINAWQIFPR-PFBOHXJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.57
• 重原子数：
  112
• 可旋转键数：
  38
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  312
• 氢给体数：
  1
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside 在 吡啶 作用下， 反应 5.0h， 以96.8%的产率得到2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->4)-6-O-acetyl-2,3-di-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthetic Studies on Glycosphingolipids from Protostomia Phyla: Synthesis of Neogala-Series Glycolipid Analogues Containing a Mannose Residue from the Earthworm Pheretima hilgendorfi.

  摘要：

  从蚯蚓 Pheretima hilgendorfi 中合成了以下两种糖磷脂类似物：三糖 2-(十四烷基)十六烷基 α-D-吡喃甘露糖基-(1→4)-β-D-吡喃半乳糖基-(1→6)-β-D-吡喃半乳糖苷 (13) 和四糖 2-(十四烷基)十六烷基 α-D-半乳糖苷-(1→6)-[α-D-吡喃甘露糖基-(1→4)]-β-D-吡喃半乳糖苷-(1→6)-β-D-吡喃半乳糖苷(20)是通过逐步缩合适当保护的单糖单元合成的。2-(trimethylsilyl)ethyl 2, 3, 4-tri-O-benzoyl-β-D-galactopyranoside 衍生物 (5) 用作糖基受体，D-半乳糖和 D-甘露糖的硫代苯衍生物分别用作供体。

  DOI：

  10.1248/cpb.47.1265
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-6-O-benzyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 18.0h， 以66.4%的产率得到2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthetic Studies on Glycosphingolipids from Protostomia Phyla: Synthesis of Neogala-Series Glycolipid Analogues Containing a Mannose Residue from the Earthworm Pheretima hilgendorfi.

  摘要：

  从蚯蚓 Pheretima hilgendorfi 中合成了以下两种糖磷脂类似物：三糖 2-(十四烷基)十六烷基 α-D-吡喃甘露糖基-(1→4)-β-D-吡喃半乳糖基-(1→6)-β-D-吡喃半乳糖苷 (13) 和四糖 2-(十四烷基)十六烷基 α-D-半乳糖苷-(1→6)-[α-D-吡喃甘露糖基-(1→4)]-β-D-吡喃半乳糖苷-(1→6)-β-D-吡喃半乳糖苷(20)是通过逐步缩合适当保护的单糖单元合成的。2-(trimethylsilyl)ethyl 2, 3, 4-tri-O-benzoyl-β-D-galactopyranoside 衍生物 (5) 用作糖基受体，D-半乳糖和 D-甘露糖的硫代苯衍生物分别用作供体。

  DOI：

  10.1248/cpb.47.1265

文献信息

• Synthetic Studies on Glycosphingolipids from Protostomia Phyla: Synthesis of Neogala-Series Glycolipid Analogues Containing a Mannose Residue from the Earthworm Pheretima hilgendorfi.
  作者：Noriyasu HADA、Akiko MATSUSAKI、Mutsumi SUGITA、Tadahiro TAKEDA

  DOI：10.1248/cpb.47.1265

  日期：——

  Two kinds of glycosphingolipid analogues from the earthworm Pheretima hilgendorfi were synthesized as follows : the trisaccharide 2-(tetradecyl)hexadecyl α-D-mannopyranosyl-(1→4)-β-D-galactopyranosyl-(1→6)-β-D-galactopyranoside (13) and the tetrasaccharide 2-(tetradecyl) hexadecyl α-D-galactopyranosyl-(1→6)-[α-D-mannopyranosyl-(1→4)]-β-D-galactopyranosyl-(1→6)-β-D-galactpyranoside (20) were synthesized by stepwise condensation of suitably protected monosaccharide units. A 2-(trimethylsilyl)ethyl 2, 3, 4-tri-O-benzoyl-β-D-galactopyranoside derivative (5) was used as the glycosyl acceptor and thiophenyl derivatives of D-galactose and D-mannose were used as donors respectively.

  从蚯蚓 Pheretima hilgendorfi 中合成了以下两种糖磷脂类似物：三糖 2-(十四烷基)十六烷基 α-D-吡喃甘露糖基-(1→4)-β-D-吡喃半乳糖基-(1→6)-β-D-吡喃半乳糖苷 (13) 和四糖 2-(十四烷基)十六烷基 α-D-半乳糖苷-(1→6)-[α-D-吡喃甘露糖基-(1→4)]-β-D-吡喃半乳糖苷-(1→6)-β-D-吡喃半乳糖苷(20)是通过逐步缩合适当保护的单糖单元合成的。2-(trimethylsilyl)ethyl 2, 3, 4-tri-O-benzoyl-β-D-galactopyranoside 衍生物 (5) 用作糖基受体，D-半乳糖和 D-甘露糖的硫代苯衍生物分别用作供体。