phenyl 4,6-O-benzylidene-3-O-methoxymethyl-1-thio-β-D-glucopyranoside | 942622-12-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 4,6-O-benzylidene-3-O-methoxymethyl-1-thio-β-D-glucopyranoside
• 英文别名: (2R,4aR,6S,7R,8R,8aR)-8-(methoxymethoxy)-2-phenyl-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-ol
• CAS: 942622-12-0
• 化学式: C₂₁H₂₄O₆S
• 分子量: 404.484
• InChiKey: NXTYUJMFRBKOQQ-UFOPBENGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  91.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 4,6-O-benzylidene-3-O-methoxymethyl-1-thio-β-D-glucopyranoside 在 吡啶 、 溶剂黄146 作用下， 反应 6.0h， 生成 phenyl 3-O-methoxymethyl-2-O-N-phenylcarbamoyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  The first total synthesis of telephiose A

  摘要：

  The first total synthesis of telephiose A (1), a novel trisaccharide ester having two acetyl groups and two benzoyl groups, was achieved by using glucosyl donor 6 and disaccharide acceptor 12. The crucial key step was the stereoselective construction of the beta-D-glucosidic linkage featuring the neighboring group participation of the 2-O-N-phenylcarbamoyl group (of donor 6), which can be selectively deprotected in the presence of acetyl and benzoyl groups. Donor 6 was prepared from D-glucose in eight steps (33% yield), whereas acceptor 12 was prepared from sucrose in six steps (35% yield). Precursors 6 and 12 were reacted in subsequent reactions (five steps) to afford 1 in 22% yield. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.138
• 作为产物：
  描述：

  苯硫酚 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 phenyl 4,6-O-benzylidene-3-O-methoxymethyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  The first total synthesis of telephiose A

  摘要：

  The first total synthesis of telephiose A (1), a novel trisaccharide ester having two acetyl groups and two benzoyl groups, was achieved by using glucosyl donor 6 and disaccharide acceptor 12. The crucial key step was the stereoselective construction of the beta-D-glucosidic linkage featuring the neighboring group participation of the 2-O-N-phenylcarbamoyl group (of donor 6), which can be selectively deprotected in the presence of acetyl and benzoyl groups. Donor 6 was prepared from D-glucose in eight steps (33% yield), whereas acceptor 12 was prepared from sucrose in six steps (35% yield). Precursors 6 and 12 were reacted in subsequent reactions (five steps) to afford 1 in 22% yield. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.138