4-methoxyphenyl (4-O-acetyl-3,6-di-O-allyl-2-O-pivaloyl-β-D-galactopyranosyl)-(1-> 4)-(3,6-di-O-allyl-2-O-pivaloyl-β-D-galactopyranosyl)-(1-> 4)-3,6-di-O-allyl-2-O-pivaloyl-β-D-galactopyranoside | 400091-39-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl (4-O-acetyl-3,6-di-O-allyl-2-O-pivaloyl-β-D-galactopyranosyl)-(1-> 4)-(3,6-di-O-allyl-2-O-pivaloyl-β-D-galactopyranosyl)-(1-> 4)-3,6-di-O-allyl-2-O-pivaloyl-β-D-galactopyranoside
• 英文别名: pivaloyl(-2)[allyl(-3)][allyl(-6)]Gal4Ac(b1-4)[pivaloyl(-2)][allyl(-3)][allyl(-6)]Gal(b1-4)[pivaloyl(-2)][allyl(-3)][allyl(-6)]Gal(b)-O-Ph(4-OMe)；[(2S,3R,4S,5S,6R)-5-[(2S,3R,4S,5S,6R)-5-acetyloxy-3-(2,2-dimethylpropanoyloxy)-4-prop-2-enoxy-6-(prop-2-enoxymethyl)oxan-2-yl]oxy-2-[(2R,3S,4S,5R,6S)-5-(2,2-dimethylpropanoyloxy)-6-(4-methoxyphenoxy)-4-prop-2-enoxy-2-(prop-2-enoxymethyl)oxan-3-yl]oxy-4-prop-2-enoxy-6-(prop-2-enoxymethyl)oxan-3-yl] 2,2-dimethylpropanoate
• CAS: 400091-39-6
• 化学式: C₆₀H₈₈O₂₁
• 分子量: 1145.35
• InChiKey: OXCYXMNXPKPHCU-RYDZXRPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  81
• 可旋转键数：
  39
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  225
• 氢给体数：
  0
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl (4-O-acetyl-3,6-di-O-allyl-2-O-pivaloyl-β-D-galactopyranosyl)-(1-> 4)-(3,6-di-O-allyl-2-O-pivaloyl-β-D-galactopyranosyl)-(1-> 4)-3,6-di-O-allyl-2-O-pivaloyl-β-D-galactopyranoside 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 19.0h， 生成 phenyl (3,6-di-O-allyl-2-O-pivaloyl-β-D-galactopyranosyl)-(1->4)-(3,6-di-O-allyl-2-O-pivaloyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-allyl-2-O-pivaloyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of linear β-(1→4)-galacto-hexa- and heptasaccharides and studies directed towards cyclogalactans

  摘要：

  Synthesis of an exclusively beta-(1-->4)-linked galactohexa- and heptasaccharide is described by coupling a 2-O-pivaloyl-3,6-O-allyl-protected thiogalactobioside donor with an equally protected. yet terminally 4-OH-free galactopentaoside. The same approach though failed to elaborate cyclic oligomers, as neither cyclodimerization of the correspondingly protected thiogalactotriosides with a 4"-OH could be effected, nor intramolecular glycosidation of the respective hexa- and heptagalactosides with an unprotected 4-OH at one. and phenylthio or sulfoxido groups at the reducing end. The causative factors underlying this are attributed to an inadequate predisposition of the linear beta-(1-->4)-galactan chains to adopt the tightly coiled molecular geometry necessary for cyclization-at least at the hexa- and heptasaccharide stage. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00081-2
• 作为产物：
  描述：

  phenyl 4-O-acetyl-3,6-di-O-allyl-2-O-pivaloyl-1-thio-β-D-galactopyranoside 、 4-methoxyphenyl 3,6-di-O-allyl-4-O-(3,6-di-O-allyl-2-O-pivaloyl-β-D-galactopyranosyl)-2-O-pivaloyl-β-D-galactopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 、 三氟甲烷磺酸甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以78%的产率得到4-methoxyphenyl (4-O-acetyl-3,6-di-O-allyl-2-O-pivaloyl-β-D-galactopyranosyl)-(1-> 4)-(3,6-di-O-allyl-2-O-pivaloyl-β-D-galactopyranosyl)-(1-> 4)-3,6-di-O-allyl-2-O-pivaloyl-β-D-galactopyranoside
  参考文献：
  名称：

  β(1→4)-连接的低聚半乳糖的定向和高效合成

  摘要：

  描述了构建 β(14)-半乳糖苷键直至六糖水平的直接、制备有效的程序。关键要素是使用苯硫基和/或苯亚砜官能团进行糖基化，以及为供体和受体等精心设计的封闭基团模式：O-2 处的新戊酰基保护以确保 β-选择性，O-3 处空间上不需要的烯丙基或苄基和 O-6 以最小化非反应性半乳糖基-4-OH 周围的空间体积，对甲氧基苯基部分，容易被 SPh 取代，作为中间异头取代基，以及用于临时保护末端 Gal-4-OH 的乙酰基. 该策略适用于供体和受体的迭代块合成和交换，从而展示了整体方法的广泛范围和通用性。

  DOI：

  10.1002/1099-0690(200110)2001:20<3849::aid-ejoc3849>3.0.co;2-q