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 | 319922-42-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Man(b1-4)[Bn(-2)][pivaloyl(-6)]Glc(b)-O-EtTMS；[(2R,3S,4S,5R,6R)-4-hydroxy-5-phenylmethoxy-6-(2-trimethylsilylethoxy)-3-[(2S,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 319922-42-4
• 化学式: C₅₇H₇₂O₁₂Si
• 分子量: 977.277
• InChiKey: CEXFEPQGCOAWFQ-LMNRBSTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.68
• 重原子数：
  70
• 可旋转键数：
  26
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  苯基-2,3,4-三-O-苄基-1-硫代-β-L-岩藻吡喃糖苷 、 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 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以65%的产率得到Bn(-2)[Bn(-3)][Bn(-4)]Fuc(a1-3)[Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Man(b1-4)][Bn(-2)][pivaloyl(-6)]Glc(b)-O-EtTMS
  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 吡啶 、 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 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

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.