2-(trimethylsilyl)ethyl 3-deoxy-4-O-<4-O-(α-D-galactopyranosyl)-β-D-galactopyranosyl>-β-D-ribo-hexopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 3-deoxy-4-O-<4-O-(α-D-galactopyranosyl)-β-D-galactopyranosyl>-β-D-ribo-hexopyranoside
• 英文别名: Gal(a1-4)Gal(b1-4)3-deoxy-D-ribHex(b)-O-EtTMS；(2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-6-[(2R,3S,5R,6R)-5-hydroxy-2-(hydroxymethyl)-6-(2-trimethylsilylethoxy)oxan-3-yl]oxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₂₃H₄₄O₁₅Si
• 分子量: 588.679
• InChiKey: NQFJPVHYJUOITK-VAIRQJBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.18
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  237
• 氢给体数：
  9
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl β-D-glucopyranoside 在 potassium fluoride 、 N-碘代丁二酰亚胺 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium methylate 、 silver trifluoromethanesulfonate 、 对甲苯磺酸 、 silver nitrate 、 溶剂黄146 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 63.67h， 生成 2-(trimethylsilyl)ethyl 3-deoxy-4-O-<4-O-(α-D-galactopyranosyl)-β-D-galactopyranosyl>-β-D-ribo-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.