2-(phenylmethoxy)-1-[(phenylmethoxy)methyl]ethyl 2,3,4,6-tetrakis-O-(phenylmethyl)-α-D-galactopyranoside | 1093661-92-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 2-(phenylmethoxy)-1-[(phenylmethoxy)methyl]ethyl 2,3,4,6-tetrakis-O-(phenylmethyl)-α-D-galactopyranoside
• 英文别名: (2S,3R,4S,5S,6R)-2-[1,3-bis(phenylmethoxy)propan-2-yloxy]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 1093661-92-7
• 化学式: C₅₁H₅₄O₈
• 分子量: 794.985
• InChiKey: JMTAHERREFESHW-SVASUFRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  59
• 可旋转键数：
  23
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(phenylmethoxy)-1-[(phenylmethoxy)methyl]ethyl 2,3,4,6-tetrakis-O-(phenylmethyl)-α-D-galactopyranoside 在 10% Pd/C 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 以100%的产率得到1,3-二羟基-2-丙基alpha-D-吡喃半乳糖苷
  参考文献：
  名称：

  Synthesis of Floridoside

  摘要：

  Floridoside (2-O-glycerol-alpha-D-galactopyranoside) is a natural glycerol glycoside found in red algae and is believed to play important roles in carbon storage, transport, and assimilation and in the regulation of osmotic balance. We describe here a rapid, high-yield, and high-stereoselectivity synthesis of floridoside in which the key step involves the 1,2-cis O-glycosylation of 1,3-dibenzylglycerol with ethyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside using iodonium dicollidine perchlorate (IDCP) or N-iodosuccinimide/trimethylsilyl triflate (NIS/TMSOTf) as promoters.

  DOI：

  10.1080/07328300802408843
• 作为产物：
  描述：

  1,3-双(苄氧基)-2-丙醇 、 乙基-2,3,4,6-O-四苄基-Beta-D-硫代半乳糖苷 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以71%的产率得到2-(phenylmethoxy)-1-[(phenylmethoxy)methyl]ethyl 2,3,4,6-tetrakis-O-(phenylmethyl)-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Floridoside

  摘要：

  Floridoside (2-O-glycerol-alpha-D-galactopyranoside) is a natural glycerol glycoside found in red algae and is believed to play important roles in carbon storage, transport, and assimilation and in the regulation of osmotic balance. We describe here a rapid, high-yield, and high-stereoselectivity synthesis of floridoside in which the key step involves the 1,2-cis O-glycosylation of 1,3-dibenzylglycerol with ethyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside using iodonium dicollidine perchlorate (IDCP) or N-iodosuccinimide/trimethylsilyl triflate (NIS/TMSOTf) as promoters.

  DOI：

  10.1080/07328300802408843

文献信息

• Synthesis of Floridoside
  作者：Michel Weïwer、Trevor Sherwood、Robert J. Linhardt

  DOI：10.1080/07328300802408843

  日期：2008.10.30

  Floridoside (2-O-glycerol-alpha-D-galactopyranoside) is a natural glycerol glycoside found in red algae and is believed to play important roles in carbon storage, transport, and assimilation and in the regulation of osmotic balance. We describe here a rapid, high-yield, and high-stereoselectivity synthesis of floridoside in which the key step involves the 1,2-cis O-glycosylation of 1,3-dibenzylglycerol with ethyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside using iodonium dicollidine perchlorate (IDCP) or N-iodosuccinimide/trimethylsilyl triflate (NIS/TMSOTf) as promoters.