2-(trimethylsilyl)ethyl 3-O-benzoyl-2-deoxy-6-O-(p-methoxybenzoyl)-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 | 176165-29-0

• 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 3-O-benzoyl-2-deoxy-6-O-(p-methoxybenzoyl)-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
• 英文别名: Gal2Ac3Ac4Ac6Ac(a1-4)[Bz(-2)][Bz(-3)]Gal6Ac(b1-4)[Bz(-3)][Bz(4-OMe)(-6)]2-deoxy-D-araHex(b)-O-EtTMS；[(2R,3S,4R,6R)-3-[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4-dibenzoyloxy-5-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-benzoyloxy-6-(2-trimethylsilylethoxy)oxan-2-yl]methyl 4-methoxybenzoate
• CAS: 176165-29-0
• 化学式: C₆₂H₇₂O₂₅Si
• 分子量: 1245.32
• InChiKey: LREYXHIYWNNROJ-UVPBBUHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.14
• 重原子数：
  88
• 可旋转键数：
  34
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  301
• 氢给体数：
  0
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 3-O-benzoyl-2-deoxy-6-O-(p-methoxybenzoyl)-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 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以88%的产率得到2-(trimethylsilyl)ethyl 2-deoxy-4-O-<4-O-(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：

  2-(trimethylsilyl)ethyl β-D-glucopyranoside 在 potassium fluoride 、 偶氮二异丁腈 、 三正丁基氢锡 、 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 吡啶 、 二氯甲烷 、 水 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 20.0h， 生成 2-(trimethylsilyl)ethyl 3-O-benzoyl-2-deoxy-6-O-(p-methoxybenzoyl)-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