3-(hexadecylsulfonyl)-2-<(hexadecylsulfonyl)methyl>propyl 3,4,6-tri-O-benzoyl-2-deoxy-β-D-arabino-hexopyranoside | 176165-36-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(hexadecylsulfonyl)-2-<(hexadecylsulfonyl)methyl>propyl 3,4,6-tri-O-benzoyl-2-deoxy-β-D-arabino-hexopyranoside
• 英文别名: [(2R,3S,4R,6R)-3,4-dibenzoyloxy-6-[3-hexadecylsulfonyl-2-(hexadecylsulfonylmethyl)propoxy]oxan-2-yl]methyl benzoate
• CAS: 176165-36-9
• 化学式: C₆₃H₉₆O₁₂S₂
• 分子量: 1109.58
• InChiKey: BLCXLXCTOYUSEC-ZWWMNCOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.6
• 重原子数：
  77
• 可旋转键数：
  47
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  182
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-(hexadecylsulfonyl)-2-<(hexadecylsulfonyl)methyl>propyl 3,4,6-tri-O-benzoyl-2-deoxy-β-D-arabino-hexopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 3-(hexadecylsulfonyl)-2-<(hexadecylsulfonyl)methyl>propyl 2-deoxy-β-D-arabino-hexopyranoside
  参考文献：
  名称：

  Synthesis of Double-Chain Bis-Sulfone Neoglycolipids of the 2-, 3-, and 6-Deoxyglobotrioses

  摘要：

  Partially protected 2-(trimethylsilyl)ethyl 2- and 3-deoxyglucosides and 6-deoxylactoside were synthesised via various routes and glycosylated with galabiosyl and galactosyl donors to give the corresponding deoxytrisaccharides. Removal of the protecting groups gave the 2-(trimethylsilyl)ethyl 2-, 3-, and 6-deoxyglobotriosides. Transformation of the protected trisaccharides into trichloroacetimidates, via the corresponding hemiacetals, proceeded in similar to 80% overall yield. Glycosylation of 3-(hexadecylsulfonyl)-2-[(hexadecylsulfonyl)methyl]propanol with the trisaccharidic trichloroacetimidates, in 72-79% yield, followed by removal of protecting groups, gave the title neoglycolipids.

  DOI：

  10.1021/jo951914k
• 作为产物：
  描述：

  3,4,6-三-O-苯甲酰基-D-葡萄糖醛 在 盐酸 、 silver silicate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 31.17h， 生成 3-(hexadecylsulfonyl)-2-<(hexadecylsulfonyl)methyl>propyl 3,4,6-tri-O-benzoyl-2-deoxy-β-D-arabino-hexopyranoside
  参考文献：
  名称：

  Synthesis of Double-Chain Bis-Sulfone Neoglycolipids of the 2-, 3-, and 6-Deoxyglobotrioses

  摘要：

  Partially protected 2-(trimethylsilyl)ethyl 2- and 3-deoxyglucosides and 6-deoxylactoside were synthesised via various routes and glycosylated with galabiosyl and galactosyl donors to give the corresponding deoxytrisaccharides. Removal of the protecting groups gave the 2-(trimethylsilyl)ethyl 2-, 3-, and 6-deoxyglobotriosides. Transformation of the protected trisaccharides into trichloroacetimidates, via the corresponding hemiacetals, proceeded in similar to 80% overall yield. Glycosylation of 3-(hexadecylsulfonyl)-2-[(hexadecylsulfonyl)methyl]propanol with the trisaccharidic trichloroacetimidates, in 72-79% yield, followed by removal of protecting groups, gave the title neoglycolipids.

  DOI：

  10.1021/jo951914k

文献信息

• Synthesis of Double-Chain Bis-Sulfone Neoglycolipids of the 2-, 3-, and 6-Deoxyglobotrioses
  作者：Zhiyuan Zhang、Göran Magnusson

  DOI：10.1021/jo951914k

  日期：1996.1.1

  Partially protected 2-(trimethylsilyl)ethyl 2- and 3-deoxyglucosides and 6-deoxylactoside were synthesised via various routes and glycosylated with galabiosyl and galactosyl donors to give the corresponding deoxytrisaccharides. Removal of the protecting groups gave the 2-(trimethylsilyl)ethyl 2-, 3-, and 6-deoxyglobotriosides. Transformation of the protected trisaccharides into trichloroacetimidates, via the corresponding hemiacetals, proceeded in similar to 80% overall yield. Glycosylation of 3-(hexadecylsulfonyl)-2-[(hexadecylsulfonyl)methyl]propanol with the trisaccharidic trichloroacetimidates, in 72-79% yield, followed by removal of protecting groups, gave the title neoglycolipids.