phenyl 2^I,3^I,2^II,3^II-tetra-O-benzyl-4^II,6^II-O-benzylidene-6^I-O-[(benzotriazol-1-yloxy)-2-carbonylbenzoyl]-1^I-thio-β-maltoside | 478549-14-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2^I,3^I,2^II,3^II-tetra-O-benzyl-4^II,6^II-O-benzylidene-6^I-O-[(benzotriazol-1-yloxy)-2-carbonylbenzoyl]-1^I-thio-β-maltoside
• 英文别名: 1-O-[[(2R,3R,4S,5R,6S)-3-[[(2R,4aR,6R,7R,8S,8aR)-2-phenyl-7,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-4,5-bis(phenylmethoxy)-6-phenylsulfanyloxan-2-yl]methyl] 2-O-(benzotriazol-1-yl) benzene-1,2-dicarboxylate
• CAS: 478549-14-3
• 化学式: C₆₇H₆₁N₃O₁₃S
• 分子量: 1148.3
• InChiKey: ZWQJKVZEKWMCIK-TZJVPSQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  84
• 可旋转键数：
  24
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  192
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  allyl 2^I,3^I,2^II,3^II-tetra-O-benzyl-6^I-O-tert-butyldiphenylsilyl-maltoside 、 phenyl 2^I,3^I,2^II,3^II-tetra-O-benzyl-4^II,6^II-O-benzylidene-6^I-O-[(benzotriazol-1-yloxy)-2-carbonylbenzoyl]-1^I-thio-β-maltoside 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到allyl 2^I,3^I,2^II,3^II-tetra-O-benzyl-6^II-O-[(2^I,3^I,2^II,3^II-tetra-O-benzyl-4^II,6^II-O-benzylidene-1^I-thio-phenyl-β-maltos-6^I-yloxy)-2-carbonylbenzoyl]-6-O-tert-butyldiphenylsilyl-1^I-O-maltoside
  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：

  phenyl 4-O-(4,6-O-benzylidene-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 sodium hydride 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 phenyl 2^I,3^I,2^II,3^II-tetra-O-benzyl-4^II,6^II-O-benzylidene-6^I-O-[(benzotriazol-1-yloxy)-2-carbonylbenzoyl]-1^I-thio-β-maltoside
  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.