2-(Trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<2-O-acetyl-3-deoxy-6-O-(p-methoxybenzoyl)-β-D-xylo-hexopyranosyl>-β-D-glucopyranoside | 172360-96-2

• 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-6-O-(p-methoxybenzoyl)-β-D-xylo-hexopyranosyl>-β-D-glucopyranoside
• 英文别名: 2-(trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-(2-O-acetyl-3-deoxy-6-O-p-methoxybenzoyl-β-D-xylo-hexopyranosyl)-β-D-glucopyranoside；Bz(4-OMe)(-6)3-deoxy-D-xylHex2Ac(b1-4)Glc2Ac3Ac6Ac(b)-O-EtTMS；[(2R,3R,5R,6S)-5-acetyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-(2-trimethylsilylethoxy)oxan-3-yl]oxy-3-hydroxyoxan-2-yl]methyl 4-methoxybenzoate
• CAS: 172360-96-2
• 化学式: C₃₃H₄₈O₁₆Si
• 分子量: 728.82
• InChiKey: IVRUFFFXVYVQBI-YXDGGYCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  50
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  198
• 氢给体数：
  1
• 氢受体数：
  16

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-6-O-(p-methoxybenzoyl)-β-D-xylo-hexopyranosyl>-β-D-glucopyranoside 在 palladium on activated charcoal 吡啶 、 2,3,5-三甲基吡啶 、 3 A molecular sieve 、 氢气 、 silver trifluoromethanesulfonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 22.5h， 生成 2,3,6-Tri-O-acetyl-4-O-<2-O-acetyl-3-deoxy-6-O-(p-methoxybenzoyl)-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-xylo-hexopyranosyl>-β-D-glucopyranose
  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 、 sodium hydrogen sulfate 、 18-冠醚-6 、 偶氮二异丁腈 、 4 A molecular sieve 、 四丁基氯化铵 、 三正丁基氢锡 、 二正丁基氧化锡 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 67.0h， 生成 2-(Trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<2-O-acetyl-3-deoxy-6-O-(p-methoxybenzoyl)-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

文献信息

• DDQ-Mediated Oxidation of 4,6-<i>O</i>-Methoxybenzylidene-Protected Saccharides in the Presence of Various Nucleophiles:  Formation of 4-OH, 6-Cl, and 6-Br Derivatives
  作者：Zhiyuan Zhang、Göran Magnusson

  DOI：10.1021/jo952177v

  日期：1996.1.1

  Treatment of 4,6-O-p-methoxybenzylidene-protected pyranosidic mono- and disaccharides with 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), in the presence of a few equivalents of water, gave the corresponding 6- and 4-O-p-methoxybenzoates with unprotected hydroxyl groups in the 4- and 6-position in the ratio similar to 4:1 and in 85-98% yield. Dry conditions in the presence of halide salts gave the 6-deoxychloro and -bromo 4-O-p-methoxybenzoates exclusively, in >90% yield.