3-(hexadecylsulfonyl)-2-<(hexadecylsulfonyl)methyl>propyl 3,6-di-O-benzoyl-2-deoxy-β-D-arabino-hexopyranoside | 176165-39-2

• 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 3,6-di-O-benzoyl-2-deoxy-β-D-arabino-hexopyranoside
• 英文别名: 3-(hexadecylsulfonyl)-2-[(hexadecylsulfonyl)methyl]propyl 3,6-di-O-benzoyl-2-deoxy-β-D-arabino-hexopyranoside；[(2R,3S,4R,6R)-4-benzoyloxy-6-[3-hexadecylsulfonyl-2-(hexadecylsulfonylmethyl)propoxy]-3-hydroxyoxan-2-yl]methyl benzoate
• CAS: 176165-39-2
• 化学式: C₅₆H₉₂O₁₁S₂
• 分子量: 1005.47
• InChiKey: OZQGGWRSSHPJMS-ZIKQCWMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.3
• 重原子数：
  69
• 可旋转键数：
  44
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  176
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  6-O-acetyl-2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-galactopyranosyl bromide 、 3-(hexadecylsulfonyl)-2-<(hexadecylsulfonyl)methyl>propyl 3,6-di-O-benzoyl-2-deoxy-β-D-arabino-hexopyranoside 在 silver silicate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以83%的产率得到3-(hexadecylsulfonyl)-2-<(hexadecylsulfonyl)methyl>propyl 3,6-di-O-benzoyl-2-deoxy-4-O-<6-O-acetyl-2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-galactopyranosyl>-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 、 sodium methylate 、 二正丁基氧化锡 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 36.22h， 生成 3-(hexadecylsulfonyl)-2-<(hexadecylsulfonyl)methyl>propyl 3,6-di-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

• Regioselective benzoylation of sugars mediated by excessive Bu2SnO: observation of temperature promoted migration
  作者：Zhiyuan Zhang、Chi-Huey Wong

  DOI：10.1016/s0040-4020(02)00661-0

  日期：2002.8

  Regioselective benzoylation of carbohydrates using an excess of dibutyltin oxide (Bu2SnO) at increased reaction temperatures has been developed for the synthesis of several glycoside benzoates with one or two free hydroxyl groups, including galactosides, glucosides, mannosides and lactosides in high yields. These compounds are useful as building blocks for the synthesis of complex saccharides and derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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.