2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzoyl-4-O-<2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-fucopyranosyl>-β-D-glucopyranoside | 172361-16-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzoyl-4-O-<2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-fucopyranosyl>-β-D-glucopyranoside
• 英文别名: Gal2Ac3Ac4Ac6Ac(a1-4)[Bz(-2)][Bz(-3)]D-Fuc(b1-4)[Bz(-2)][Bz(-3)][Bz(-6)]Glc(b)-O-EtTMS；[(2R,3R,4S,5R,6R)-4,5-dibenzoyloxy-3-[(2S,3R,4S,5S,6R)-3,4-dibenzoyloxy-6-methyl-5-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-(2-trimethylsilylethoxy)oxan-2-yl]methyl benzoate
• CAS: 172361-16-9
• 化学式: C₆₆H₇₂O₂₄Si
• 分子量: 1277.37
• InChiKey: ZRKKMDAHFWGPQX-FDENTMTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.42
• 重原子数：
  91
• 可旋转键数：
  33
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  292
• 氢给体数：
  0
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzoyl-4-O-<2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-fucopyranosyl>-β-D-glucopyranoside 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到2,3,6-Tri-O-benzoyl-4-O-<2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-fucopyranosyl>-β-D-glucopyranoside
  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 deoxylactosides (deoxygenated in the 2-, 3-, and 6-positions of the galactose unit) were synthesized via various routes and glycosylated with 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 86-96% overall yield. Glycosylation of 3-(hexadecylsulfonyl)-2-[(hexadecylsulfonyl)methyl]propanol with the trisaccharidic trichloroacetimidates, in 37-68% yield, followed by removal of protecting groups, gave the title neoglycolipids.

  DOI：

  10.1021/jo00127a042
• 作为产物：
  描述：

  乙酸酐 、 2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzoyl-4-O-<2,3-di-O-benzoyl-4-O-(α-D-galactopyranosyl)-β-D-fucopyranosyl>-β-D-glucopyranoside 在 吡啶 作用下， 反应 20.0h， 以97%的产率得到2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzoyl-4-O-<2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-fucopyranosyl>-β-D-glucopyranoside
  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 deoxylactosides (deoxygenated in the 2-, 3-, and 6-positions of the galactose unit) were synthesized via various routes and glycosylated with 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 86-96% overall yield. Glycosylation of 3-(hexadecylsulfonyl)-2-[(hexadecylsulfonyl)methyl]propanol with the trisaccharidic trichloroacetimidates, in 37-68% yield, followed by removal of protecting groups, gave the title neoglycolipids.

  DOI：

  10.1021/jo00127a042