(2R,3R,4S,5S,6R)-3-Benzyloxy-6-hydroxymethyl-2-(2-trimethylsilanyl-ethoxy)-5-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-ol | 319922-40-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5S,6R)-3-Benzyloxy-6-hydroxymethyl-2-(2-trimethylsilanyl-ethoxy)-5-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-ol
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Man(b1-4)[Bn(-2)]Glc(b)-O-EtTMS；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-5-phenylmethoxy-6-(2-trimethylsilylethoxy)-3-[(2S,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-4-ol
• CAS: 319922-40-2
• 化学式: C₅₂H₆₄O₁₁Si
• 分子量: 893.159
• InChiKey: BOYNNWAMQSPSMG-SPBQYHHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.09
• 重原子数：
  64
• 可旋转键数：
  23
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  三甲基乙酰氯 、 (2R,3R,4S,5S,6R)-3-Benzyloxy-6-hydroxymethyl-2-(2-trimethylsilanyl-ethoxy)-5-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-ol 在 吡啶 作用下， 以57%的产率得到2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-5-benzyloxy-4-hydroxy-6-(2-trimethylsilanyl-ethoxy)-3-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Synthetic studies on novel fucosylated glycosphingolipids from the millipede, Parafontaria laminata armigera

  摘要：

  A novel glycosphingolipid, beta -D-Manp-(1 -->4)-[(alpha -L-Fucp-(1 -->3)]-beta -D-Glcp-(1 -->1)-Cer, from the millipede, Parafontaria laminata armigera, was synthesized. A key reaction of this synthetic procedure is the formation of a spiro-orthoester and its reduction for p-selective mannosylation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01603-8
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone 在 lithium aluminium tetrahydride 、 三氯化铝 、 甲氧基三甲基硅烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 (2R,3R,4S,5S,6R)-3-Benzyloxy-6-hydroxymethyl-2-(2-trimethylsilanyl-ethoxy)-5-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-ol
  参考文献：
  名称：

  Synthetic studies on novel fucosylated glycosphingolipids from the millipede, Parafontaria laminata armigera

  摘要：

  A novel glycosphingolipid, beta -D-Manp-(1 -->4)-[(alpha -L-Fucp-(1 -->3)]-beta -D-Glcp-(1 -->1)-Cer, from the millipede, Parafontaria laminata armigera, was synthesized. A key reaction of this synthetic procedure is the formation of a spiro-orthoester and its reduction for p-selective mannosylation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01603-8

文献信息

• Synthetic studies on novel fucosylated glycosphingolipids from the millipede, Parafontaria laminata armigera
  作者：Noriyasu Hada、Isao Ohtsuka、Mutsumi Sugita、Tadahiro Takeda

  DOI：10.1016/s0040-4039(00)01603-8

  日期：2000.11

  A novel glycosphingolipid, beta -D-Manp-(1 -->4)-[(alpha -L-Fucp-(1 -->3)]-beta -D-Glcp-(1 -->1)-Cer, from the millipede, Parafontaria laminata armigera, was synthesized. A key reaction of this synthetic procedure is the formation of a spiro-orthoester and its reduction for p-selective mannosylation. (C) 2000 Elsevier Science Ltd. All rights reserved.