O-(4,5,6,8-tetra-O-benzyl-1,2-dideoxy-α-D-gluco-oct-3-ulo-1-enopyranosyl)-N-tert-butoxycarbonyl-L-serine methyl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: O-(4,5,6,8-tetra-O-benzyl-1,2-dideoxy-α-D-gluco-oct-3-ulo-1-enopyranosyl)-N-tert-butoxycarbonyl-L-serine methyl ester
• 英文别名: methyl (2S)-3-[(2S,3R,4S,5R,6R)-2-ethenyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• 化学式: C₄₅H₅₃NO₁₀
• 分子量: 767.917
• InChiKey: AZULDTWXMVBQJS-OQPVRTLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  56
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (Z)-2-((3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ylidene)ethan-1-ol 在 三氯化铝 、 4 A molecular sieve 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.67h， 生成 O-(4,5,6,8-tetra-O-benzyl-1,2-dideoxy-α-D-gluco-oct-3-ulo-1-enopyranosyl)-N-tert-butoxycarbonyl-L-serine methyl ester
  参考文献：
  名称：

  Inter- and intramolecular glycosylation of exo-glycals promoted by metallic Lewis acids

  摘要：

  exo-Glycosyl carbonates were employed for inter- and intramolecular glycosylation reactions. A number of metallic Lewis Acids and solvents were examined to enhance the reactivity. The optimum conditions were found to be the use of AlCl3 in 1-nitropropane. The method was demonstrated to be useful for the intermolecular glycosyl transfer of several nucleophiles, including simple alcohols, sugars, and amino acid derivatives; however, intramolecular glycosylations were not successful. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.04.003