3-O-benzyl-5,6-di-O-tetradecyl-D-glucitol | 350243-22-0

• 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: 3-O-benzyl-5,6-di-O-tetradecyl-D-glucitol
• 英文别名: (2S,3R,4R,5R)-3-phenylmethoxy-5,6-di(tetradecoxy)hexane-1,2,4-triol
• CAS: 350243-22-0
• 化学式: C₄₁H₇₆O₆
• 分子量: 665.051
• InChiKey: SWZKZGBHVVWUNF-HPVVNECPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  47
• 可旋转键数：
  36
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-5,6-di-O-tetradecyl-D-glucitol 在 palladium dihydroxide 、 三氟甲磺酸三甲基硅酯 、 环己烯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 1-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-5,6-di-O-tetradecyl-D-glucitol
  参考文献：
  名称：

  Syntheses of neoglycolipids with hexitol spacers between the saccharidic and the lipidic parts

  摘要：

  Four neoglycolipids having 2-amino-2-deoxy-D-glucose or D-galactose moieties linked to the lipidic parr by a glucitol or a mannitol spacer-arm have been synthesized. The key step of the synthetic strategy was the regiospecific or regioselective beta -glycosylation of partially protected glucitol or mannitol accepters by either 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-alpha -D-mannopyranosyl azide or 2,3,4,6-tetra-O-benzoyl-alpha -D-galactopyranosyl trichloroacetimidate donors. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00019-2
• 作为产物：
  描述：

  (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 在 sodium hydroxide 、 sodium tetrahydroborate 、 硫酸 、 四丁基溴化铵 作用下， 以 1,4-二氧六环 、 乙醇 、 氯仿 、 水 为溶剂， 反应 24.5h， 生成 3-O-benzyl-5,6-di-O-tetradecyl-D-glucitol
  参考文献：
  名称：

  Syntheses of neoglycolipids with hexitol spacers between the saccharidic and the lipidic parts

  摘要：

  Four neoglycolipids having 2-amino-2-deoxy-D-glucose or D-galactose moieties linked to the lipidic parr by a glucitol or a mannitol spacer-arm have been synthesized. The key step of the synthetic strategy was the regiospecific or regioselective beta -glycosylation of partially protected glucitol or mannitol accepters by either 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-alpha -D-mannopyranosyl azide or 2,3,4,6-tetra-O-benzoyl-alpha -D-galactopyranosyl trichloroacetimidate donors. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00019-2

文献信息

• Syntheses of neoglycolipids with hexitol spacers between the saccharidic and the lipidic parts
  作者：Dominique Lafont、Barbara Gross、Rene Kleinegesse、Fabienne Dumoulin、Paul Boullanger

  DOI：10.1016/s0008-6215(01)00019-2

  日期：2001.3

  Four neoglycolipids having 2-amino-2-deoxy-D-glucose or D-galactose moieties linked to the lipidic parr by a glucitol or a mannitol spacer-arm have been synthesized. The key step of the synthetic strategy was the regiospecific or regioselective beta -glycosylation of partially protected glucitol or mannitol accepters by either 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-alpha -D-mannopyranosyl azide or 2,3,4,6-tetra-O-benzoyl-alpha -D-galactopyranosyl trichloroacetimidate donors. (C) 2001 Elsevier Science Ltd. All rights reserved.