phenyl 3,4-di-O-benzyl-1-thio-β-D-glucopyranoside | 1004556-12-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3,4-di-O-benzyl-1-thio-β-D-glucopyranoside
• 英文别名: (2S,3R,4R,5R,6R)-6-(hydroxymethyl)-4,5-bis(phenylmethoxy)-2-phenylsulfanyloxan-3-ol
• CAS: 1004556-12-0
• 化学式: C₂₆H₂₈O₅S
• 分子量: 452.571
• InChiKey: GIYBVULYFUXSTM-SDVOOXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  93.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 3,4-di-O-benzyl-1-thio-β-D-glucopyranoside 在 氢氧化钾 、 sodium tetrahydroborate 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 Angstroem MS 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (11S)-11-[(2R,3R,4S,5R,6R)-3-[(2S,3R,4R,5R,6R)-3-hydroxy-4-[(2S,3R,4R,5R,6R)-3-hydroxy-6-methyl-5-phenylmethoxy-4-prop-2-enoxyoxan-2-yl]oxy-6-methyl-5-phenylmethoxyoxan-2-yl]oxy-6-methyl-4,5-bis(phenylmethoxy)oxan-2-yl]oxytetradecanoic acid
  参考文献：
  名称：

  Total synthesis of calonyctin A2, a macrolidic glycolipid with plant growth-promoting activity

  摘要：

  Calonyctin A2, a tetrasaccharidic glycolipid having a 22-membered macrolidic structure, has been synthesized by the assembly of three 6-deoxygenated thioglycoside intermediates. The short-step synthesis was achieved by preparation of the most complicated b-c disaccharide unit from phenyl 2,2':4,6:4',6'-tri-O-benzylidene-1-thio-beta-D-laminaribioside without any glycosidation reaction and by regioselective macrolactonization. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00427-5
• 作为产物：
  描述：

  phenyl 4,6-O-benzylidene-3-O-benzyl-1-thio-β-glucopyranoside 生成 phenyl 3,4-di-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Total synthesis of calonyctin A2, a macrolidic glycolipid with plant growth-promoting activity

  摘要：

  Calonyctin A2, a tetrasaccharidic glycolipid having a 22-membered macrolidic structure, has been synthesized by the assembly of three 6-deoxygenated thioglycoside intermediates. The short-step synthesis was achieved by preparation of the most complicated b-c disaccharide unit from phenyl 2,2':4,6:4',6'-tri-O-benzylidene-1-thio-beta-D-laminaribioside without any glycosidation reaction and by regioselective macrolactonization. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00427-5

文献信息

• Tandem Catalysis for a One-Pot Regioselective Protection of Carbohydrates: The Example of Glucose
  作者：Antoine Français、Dominique Urban、Jean-Marie Beau

  DOI：10.1002/anie.200703437

  日期：2007.11.19