phenyl O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1-4)-O[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)]-2,6-di-O-benzoyl-1-thio-β-D-glucopyranoside | 195712-30-2

• 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: phenyl O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1-4)-O[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)]-2,6-di-O-benzoyl-1-thio-β-D-glucopyranoside
• 英文别名: [(3aS,4R,6S,7R,7aS)-7-benzoyloxy-6-[(2R,3R,4S,5R,6S)-5-benzoyloxy-2-(benzoyloxymethyl)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-6-phenylsulfanyloxan-3-yl]oxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl benzoate
• CAS: 195712-30-2
• 化学式: C₇₆H₇₄O₁₈S
• 分子量: 1307.48
• InChiKey: LEATYDWVOFEJGP-JTGUQULLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.1
• 重原子数：
  95
• 可旋转键数：
  29
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  223
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  2-tetradecylhexadecan-1-ol 、 phenyl O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1-4)-O[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)]-2,6-di-O-benzoyl-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 氯仿 为溶剂， 以86%的产率得到2-tetradecylhexadecyl O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1-4)-O-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)]-2,6-di-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  A Highly Practical Synthesis of Sulfated Lewis X:  One-Pot, Two-Step Glycosylation Using “Armed/Disarmed” Coupling and Selective Benzoylation and Sulfation

  摘要：

  In spite of the several attractive biological activities of the Le(x), sLe(x), and sulfated Le(x) derivatives, there are still limitations in their practical syntheses. One of the most difficult problems is the many steps required for their syntheses. Therefore, we investigated simple constructions of the Le(x) analogs and succeeded in establishing highly practical syntheses of the Le(x) and sulfated Le(x) analogs. Especially, the ''armed/disarmed'' method allowed the first synthesis of Le(x) derivatives by a one-pot, two-step glycosylation. This synthetic strategy could be an applicable and useful method for oligosaccharide constructions of Le(x), sulfated Le(x), and other derivatives.

  DOI：

  10.1021/jo970076m
• 作为产物：
  描述：

  phenyl (3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-1-thio-β-D-glucopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 7.0h， 生成 phenyl O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1-4)-O[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)]-2,6-di-O-benzoyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  A Highly Practical Synthesis of Sulfated Lewis X:  One-Pot, Two-Step Glycosylation Using “Armed/Disarmed” Coupling and Selective Benzoylation and Sulfation

  摘要：

  In spite of the several attractive biological activities of the Le(x), sLe(x), and sulfated Le(x) derivatives, there are still limitations in their practical syntheses. One of the most difficult problems is the many steps required for their syntheses. Therefore, we investigated simple constructions of the Le(x) analogs and succeeded in establishing highly practical syntheses of the Le(x) and sulfated Le(x) analogs. Especially, the ''armed/disarmed'' method allowed the first synthesis of Le(x) derivatives by a one-pot, two-step glycosylation. This synthetic strategy could be an applicable and useful method for oligosaccharide constructions of Le(x), sulfated Le(x), and other derivatives.

  DOI：

  10.1021/jo970076m

文献信息

• A Highly Practical Synthesis of Sulfated Lewis X:  One-Pot, Two-Step Glycosylation Using “Armed/Disarmed” Coupling and Selective Benzoylation and Sulfation
  作者：Takahiro Tsukida、Masahiro Yoshida、Kiriko Kurokawa、Yoshiyuki Nakai、Toshio Achiha、Takao Kiyoi、Hirosato Kondo

  DOI：10.1021/jo970076m

  日期：1997.10.1

  In spite of the several attractive biological activities of the Le(x), sLe(x), and sulfated Le(x) derivatives, there are still limitations in their practical syntheses. One of the most difficult problems is the many steps required for their syntheses. Therefore, we investigated simple constructions of the Le(x) analogs and succeeded in establishing highly practical syntheses of the Le(x) and sulfated Le(x) analogs. Especially, the ''armed/disarmed'' method allowed the first synthesis of Le(x) derivatives by a one-pot, two-step glycosylation. This synthetic strategy could be an applicable and useful method for oligosaccharide constructions of Le(x), sulfated Le(x), and other derivatives.