2-(Trimethylsilyl)ethyl 2-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranoside | 197143-98-9

• 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-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranoside
• 英文别名: 2-(Trimethylsilyl)ethyl 2-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl)-beta-D-xylopyranoside；[(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[(3R,4S,5R,6S)-5-benzoyloxy-4-hydroxy-6-(2-trimethylsilylethoxy)oxan-3-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 197143-98-9
• 化学式: C₅₁H₅₂O₁₅Si
• 分子量: 933.05
• InChiKey: DMEWFAXOWQGDRO-NBGXLMAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.93
• 重原子数：
  67
• 可旋转键数：
  22
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  189
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  2-(Trimethylsilyl)ethyl 2-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranoside 、 乙酸酐 在 甲苯 、 SiO2 、 toluene-ethyl acetate 作用下， 以 吡啶 为溶剂， 以to give 4 (28.9 mg, 99%)的产率得到2-(Trimethylsilyl)ethyl 3-O-acetyl-2-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranoside
  参考文献：
  名称：

  Antiproliferative Compositions Comprising Aryl Substituted Xylopyranoside Derivatives

  摘要：

  该专利涉及一种新的木糖基糖苷化合物，该化合物将木糖与含有多个芳香环的糖苷原通过O-, S-或C-糖苷键连接，以及包含新的木糖基糖苷和非木糖基抗肿瘤剂、药物或膳食补充剂的组合物。这些化合物或组合物用于治疗增生性疾病，包括各种形式的癌症。

  公开号：

  US20080027023A1
• 作为产物：
  描述：

  2,3,4-三-O-乙酰基-α-D-木吡喃糖苷溴 在 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 MS 300AW 、 四丁基氟化铵 、 sodium methylate 、 溶剂黄146 、 三乙胺 、 mercury dibromide 、 mercury(II) oxide 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 70.25h， 生成 2-(Trimethylsilyl)ethyl 2-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranoside
  参考文献：
  名称：

  Synthesis of XylβCer, Galβ1−4XylβCer, NeuAcα2−3Galβ1−4XylβCer and the Corresponding Lactone and Lactam Trisaccharides

  摘要：

  2-(Trimethylsilyl)ethyl 2-O-benzoyl- and 2,3-di-O-acetyl-beta-D-xylopyranosides (12 and 14) were synthesized in high yields and subjected to glycosylation with various glycosyl donors. Galactosylation of 12 gave the xylose analogue of TMSEt lactoside (3), which was transformed into the glycosyl acceptor 19. Sialylation then gave the xylose analogue of G(M3) trisaccharide (5). The TMSEt glycosides 10, 25, and 32 were transformed into the corresponding trichloroacetimidates, which were used for glycosylation of an azidosphingosine derivative. The resulting sphingosyl glycosides were transformed into the title ceramides. Treatment of NeuAc alpha 2-3Gal beta 1-4Xyl beta Cer (5) with acetic acid gave the corresponding l''-2'-lactone 7. Glycosylation of 12 or 14 with a G(M4)-lactam donor (40) gave the xylose analogue of G(M3)-lactam (42). There was a 3-fold increase in the formation of GAG chains in the presence of 0.5 mu M Xyl beta Cer (2) in the medium.

  DOI：

  10.1021/jo970298k

文献信息

• Synthesis of XylβCer, Galβ1−4XylβCer, NeuAcα2−3Galβ1−4XylβCer and the Corresponding Lactone and Lactam Trisaccharides
  作者：Michael Wilstermann、Göran Magnusson

  DOI：10.1021/jo970298k

  日期：1997.11.1

  2-(Trimethylsilyl)ethyl 2-O-benzoyl- and 2,3-di-O-acetyl-beta-D-xylopyranosides (12 and 14) were synthesized in high yields and subjected to glycosylation with various glycosyl donors. Galactosylation of 12 gave the xylose analogue of TMSEt lactoside (3), which was transformed into the glycosyl acceptor 19. Sialylation then gave the xylose analogue of G(M3) trisaccharide (5). The TMSEt glycosides 10, 25, and 32 were transformed into the corresponding trichloroacetimidates, which were used for glycosylation of an azidosphingosine derivative. The resulting sphingosyl glycosides were transformed into the title ceramides. Treatment of NeuAc alpha 2-3Gal beta 1-4Xyl beta Cer (5) with acetic acid gave the corresponding l''-2'-lactone 7. Glycosylation of 12 or 14 with a G(M4)-lactam donor (40) gave the xylose analogue of G(M3)-lactam (42). There was a 3-fold increase in the formation of GAG chains in the presence of 0.5 mu M Xyl beta Cer (2) in the medium.
• Antiproliferative Compositions Comprising Aryl Substituted Xylopyranoside Derivatives
  申请人：Ellervik Ulf

  公开号：US20080027023A1

  公开（公告）日：2008-01-31

  Novel xylose based glycoside compounds that have xylose linked O-, S- or C-glycosidically to an aglycone containing several aromatic rings, and compositions that comprise the novel xylose based glycosides and non-xylose-based anti-tumor agents, pharmaceuticals or dietary supplements. The compounds or compositions are administered to treat proliferative diseases, including various forms of cancer.

  本发明涉及一种新型木糖基糖苷化合物，其将木糖与一个含有多个芳香环的无糖基连接，其中连接方式为O-, S-或C-糖苷化。此外，还提供了包含这种新型木糖基糖苷化合物和非木糖基抗肿瘤药物、药品或膳食补充剂的组合物。这些化合物或组合物可用于治疗增殖性疾病，包括各种癌症。