phenyl (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-1-thio-β-D-galactopyranoside | 503312-94-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl (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-1-thio-β-D-galactopyranoside
• CAS: 503312-94-5
• 化学式: C₅₉H₈₆O₁₉S
• 分子量: 1131.39
• InChiKey: VNVWTCYZIAYACH-XGNFDVIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.85
• 重原子数：
  79.0
• 可旋转键数：
  31.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  206.73
• 氢给体数：
  0.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  phenyl (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-1-thio-β-D-galactopyranoside 在 水 、 双氧水 、 sodium methylate 、 乙酸酐 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 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-β-D-galactopyranosyl sulfoxide
  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：

  苯基硫三甲基硅烷 、 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 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以88%的产率得到phenyl (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-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