4,5,6,8-tetra-O-benzyl-1,2-dideoxy-α-D-gluco-oct-3-ulo-1-enopyranosyl-(3->6)-1,2:3,4-diisopropylidine-α-D-galactopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,5,6,8-tetra-O-benzyl-1,2-dideoxy-α-D-gluco-oct-3-ulo-1-enopyranosyl-(3->6)-1,2:3,4-diisopropylidine-α-D-galactopyranose
• 英文别名: (1S,2R,6R,8R,9S)-8-[[(2S,3R,4S,5R,6R)-2-ethenyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxymethyl]-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• 化学式: C₄₈H₅₆O₁₁
• 分子量: 808.966
• InChiKey: FJNWHBWHWCYIES-WSRDLLSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  59
• 可旋转键数：
  17
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  11

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 4,5,6,8-tetra-O-benzyl-1,2-dideoxy-α-D-gluco-oct-3-ulo-1-enopyranosyl-(3->6)-1,2:3,4-diisopropylidine-α-D-galactopyranose
  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

文献信息

• Inter- and intramolecular glycosylation of exo-glycals promoted by metallic Lewis acids
  作者：Sheng-Jie Hsu、Hui-Chang Lin、Chun-Hung Lin

  DOI：10.1016/j.carres.2006.04.003

  日期：2006.7

  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.