phenyl 4^II,6^II-O-benzylidene-6^I-O-tert-butyldiphenylsilyl-1^I-thio-β-maltotrioside | 478549-28-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 4^II,6^II-O-benzylidene-6^I-O-tert-butyldiphenylsilyl-1^I-thio-β-maltotrioside
• 英文别名: (2R,4aR,6R,7R,8R,8aS)-6-[(2R,3S,4R,5R,6R)-6-[(2R,3S,4R,5R,6S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-4,5-dihydroxy-6-phenylsulfanyloxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 478549-28-9
• 化学式: C₄₇H₅₈O₁₅SSi
• 分子量: 923.12
• InChiKey: WSKRJKRLZUWDNQ-AGRGPDMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  64
• 可旋转键数：
  14
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  241
• 氢给体数：
  7
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 phenyl 4^II,6^II-O-benzylidene-6^I-O-tert-butyldiphenylsilyl-1^I-thio-β-maltotrioside 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以94%的产率得到phenyl 2^I,3^I,2^II,3^II,6^II,2^III,3^III-hepta-O-benzyl-4^II,6^II-O-benzylidene-6^I-O-tert-butyldiphenylsilyl-1^I-thio-β-maltotrioside
  参考文献：
  名称：

  Chemical Synthesis of Cyclodextrins by Using Intramolecular Glycosylation

  摘要：

  An efficient synthesis of cyclodextrins (CDs) by using the intramolecular glycosylation is demonstrated. alpha-CD, an alpha(1-->4)linked hexaglucoside, was prepared via a block condensation of three maltose units. A modified key maltose intermediate as a precursor to both glycosyl donor and acceptor components was prepared in 6 steps starting from maltose. All the glycosylation for chain elongation and cyclization of saccharides was carried out after tethering the donor to the acceptor by the phthaloyl bridge to give the desired saccharides in good yields with complete alpha-selectivity. delta-CD composed of 9 glucose units was synthesized by the same manner from three maltotriose units.

  DOI：

  10.1021/jo025887r
• 作为产物：
  描述：

  maltotriose peracetate 在 吡啶 、 4-二甲氨基吡啶 、 sodium methylate 、 对甲苯磺酸 、 zinc(II) iodide 作用下， 以 甲醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~60.0 ℃ 、2.0 kPa 条件下， 反应 7.0h， 生成 phenyl 4^II,6^II-O-benzylidene-6^I-O-tert-butyldiphenylsilyl-1^I-thio-β-maltotrioside
  参考文献：
  名称：

  Chemical Synthesis of Cyclodextrins by Using Intramolecular Glycosylation

  摘要：

  An efficient synthesis of cyclodextrins (CDs) by using the intramolecular glycosylation is demonstrated. alpha-CD, an alpha(1-->4)linked hexaglucoside, was prepared via a block condensation of three maltose units. A modified key maltose intermediate as a precursor to both glycosyl donor and acceptor components was prepared in 6 steps starting from maltose. All the glycosylation for chain elongation and cyclization of saccharides was carried out after tethering the donor to the acceptor by the phthaloyl bridge to give the desired saccharides in good yields with complete alpha-selectivity. delta-CD composed of 9 glucose units was synthesized by the same manner from three maltotriose units.

  DOI：

  10.1021/jo025887r

文献信息

• Chemical Synthesis of Cyclodextrins by Using Intramolecular Glycosylation
  作者：Masahiro Wakao、Koichi Fukase、Shoichi Kusumoto

  DOI：10.1021/jo025887r

  日期：2002.11.1

  An efficient synthesis of cyclodextrins (CDs) by using the intramolecular glycosylation is demonstrated. alpha-CD, an alpha(1-->4)linked hexaglucoside, was prepared via a block condensation of three maltose units. A modified key maltose intermediate as a precursor to both glycosyl donor and acceptor components was prepared in 6 steps starting from maltose. All the glycosylation for chain elongation and cyclization of saccharides was carried out after tethering the donor to the acceptor by the phthaloyl bridge to give the desired saccharides in good yields with complete alpha-selectivity. delta-CD composed of 9 glucose units was synthesized by the same manner from three maltotriose units.