2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(3,6-di-O-benzoyl-2-deoxy-β-D-lyxo-hexopyranosyl)-β-D-glucopyranoside | 172360-79-1

• 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-benzyl-4-O-(3,6-di-O-benzoyl-2-deoxy-β-D-lyxo-hexopyranosyl)-β-D-glucopyranoside
• 英文别名: Bz(-3)[Bz(-6)]2-deoxy-D-lyxHex(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]Glc(b)-O-EtTMS；[(2R,3R,4R,6S)-4-benzoyloxy-6-[(2R,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-3-yl]oxy-3-hydroxyoxan-2-yl]methyl benzoate
• CAS: 172360-79-1
• 化学式: C₅₂H₆₀O₁₂Si
• 分子量: 905.127
• InChiKey: HBVPRAZDGMEKBI-VVHKKNKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  65
• 可旋转键数：
  23
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran 、 2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(3,6-di-O-benzoyl-2-deoxy-β-D-lyxo-hexopyranosyl)-β-D-glucopyranoside 在 2,3,5-三甲基吡啶 、 3 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-<3,6-di-O-benzoyl-2-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-lyxo-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：

  6-O-benzoyl-3,4-di-O-isopropylidene-D-galactal 在 palladium on activated charcoal N-碘代丁二酰亚胺 、 氢气 、 二正丁基氧化锡 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 乙酸乙酯 、 乙腈 为溶剂， 反应 45.0h， 生成 2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(3,6-di-O-benzoyl-2-deoxy-β-D-lyxo-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

文献信息

• Synthesis of Double-Chain Bis-sulfone Neoglycolipids of the 2'-, 3'-, and 6'-Deoxyglobotrioses
  作者：Zhiyuan Zhang、Goeran Magnusson

  DOI：10.1021/jo00127a042

  日期：1995.11

  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.