Benzoic acid (E)-(R)-1-{(S)-2-[(2R,3R,4S,5R)-3,4-diacetoxy-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-1-octadecanoylamino-ethyl}-hexadec-2-enyl ester | 197144-09-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: Benzoic acid (E)-(R)-1-{(S)-2-[(2R,3R,4S,5R)-3,4-diacetoxy-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-1-octadecanoylamino-ethyl}-hexadec-2-enyl ester
• 英文别名: [(E,2S,3R)-1-[(2R,3R,4S,5R)-3,4-diacetyloxy-5-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-(octadecanoylamino)octadec-4-en-3-yl] benzoate
• CAS: 197144-09-5
• 化学式: C₆₆H₁₀₅NO₁₉
• 分子量: 1216.56
• InChiKey: UJAPABZEQDWFMV-LBLNACFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16
• 重原子数：
  86
• 可旋转键数：
  52
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  250
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  Benzoic acid (E)-(R)-1-{(S)-2-[(2R,3R,4S,5R)-3,4-diacetoxy-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-1-octadecanoylamino-ethyl}-hexadec-2-enyl ester 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以95%的产率得到Octadecanoic acid {(E)-(1S,2R)-1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxymethyl]-2-hydroxy-heptadec-3-enyl}-amide
  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
• 作为产物：
  描述：

  Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(3R,4S,5R,6S)-4,5-diacetoxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester 在 MS 300AW 、 三氟化硼乙醚 、 硫化氢 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 128.5h， 生成 Benzoic acid (E)-(R)-1-{(S)-2-[(2R,3R,4S,5R)-3,4-diacetoxy-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-1-octadecanoylamino-ethyl}-hexadec-2-enyl ester
  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