2-(Trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<2-O-acetyl-3-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-xylo-hexopyranosyl>-β-D-glucopyranoside | 172361-04-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(Trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<2-O-acetyl-3-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-xylo-hexopyranosyl>-β-D-glucopyranoside
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(a1-4)3-deoxy-D-xylHex2Ac(b1-4)Glc2Ac3Ac6Ac(b)-O-EtTMS；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-3-[(2S,3R,5R,6R)-3-acetyloxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-(2-trimethylsilylethoxy)oxan-2-yl]methyl acetate
• CAS: 172361-04-5
• 化学式: C₅₉H₇₆O₁₉Si
• 分子量: 1117.33
• InChiKey: JPCKUQCVYMNSEC-BDKYPYJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.0
• 重原子数：
  79
• 可旋转键数：
  31
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  218
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  2-(Trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<2-O-acetyl-3-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-xylo-hexopyranosyl>-β-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 10.0h， 以92%的产率得到2-(Trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<2-O-acetyl-3-deoxy-4-O-(α-D-galactopyranosyl)-β-D-xylo-hexopyranosyl>-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：

  2-(Trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<2-O-acetyl-3-deoxy-β-D-xylo-hexopyranosyl>-β-D-glucopyranoside 在 咪唑 、 2,3,5-三甲基吡啶 、 3 A molecular sieve 、 四丁基氟化铵 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 2-(Trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<2-O-acetyl-3-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-xylo-hexopyranosyl>-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