2-(Trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<2-O-acetyl-6-O-(tert-butyldimethylsilyl)-3-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-xylo-hexopyranosyl>-β-D-glucopyranoside | 172361-03-4

• 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-acetyl-4-O-<2-O-acetyl-6-O-(tert-butyldimethylsilyl)-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)[TBDMS(-6)]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-[[tert-butyl(dimethyl)silyl]oxymethyl]-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: 172361-03-4
• 化学式: C₆₅H₉₀O₁₉Si₂
• 分子量: 1231.59
• InChiKey: USMNJRKRCOBTEK-PZQZLDLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.03
• 重原子数：
  86
• 可旋转键数：
  34
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  207
• 氢给体数：
  0
• 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-6-O-(tert-butyldimethylsilyl)-3-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-xylo-hexopyranosyl>-β-D-glucopyranoside 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 以99%的产率得到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
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 4-O-(4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 在 吡啶 、 咪唑 、 2,3,5-三甲基吡啶 、 偶氮二异丁腈 、 3 A molecular sieve 、 四丁基氯化铵 、 三正丁基氢锡 、 silver trifluoromethanesulfonate 、 二正丁基氧化锡 、 溶剂黄146 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 78.5h， 生成 2-(Trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<2-O-acetyl-6-O-(tert-butyldimethylsilyl)-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