phenyl 3-O-methoxymethyl-2-O-N-phenylcarbamoyl-1-thio-β-D-glucopyranoside | 942622-14-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3-O-methoxymethyl-2-O-N-phenylcarbamoyl-1-thio-β-D-glucopyranoside
• 英文别名: [(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-4-(methoxymethoxy)-2-phenylsulfanyloxan-3-yl] N-phenylcarbamate
• CAS: 942622-14-2
• 化学式: C₂₁H₂₅NO₇S
• 分子量: 435.498
• InChiKey: AVOWTFDBIJFPCC-OBKDMQGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phenyl 3-O-methoxymethyl-2-O-N-phenylcarbamoyl-1-thio-β-D-glucopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 MS 4 Angstroem 、 N,N-二异丙基乙胺 、 四丁基亚硝酸铵 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 6,1'-di-O-acetyl-4,3'-di-O-benzoyl-3-O-methoxymethyl-2-O-(3,4,6-tri-O-methoxymethyl-β-D-glucopyranosyl)-4',6'-O-tetraisopropyldisiloxanilidene sucrose
  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：

  苯基-4,6-O-苯亚甲基-1-硫代-Β-D-吡喃葡萄糖苷 在 吡啶 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 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

文献信息

• The first total synthesis of telephiose A
  作者：Ken-ichi Sato、Koudai Sakai、Keiko Tsushima、Shoji Akai

  DOI：10.1016/j.tetlet.2007.03.138

  日期：2007.5

  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.