phenyl 2-O-acetyl-3,4-di-O-benzyl-6-O-mesyl-1-thio-β-D-glucopyranoside | 261926-70-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-O-acetyl-3,4-di-O-benzyl-6-O-mesyl-1-thio-β-D-glucopyranoside
• 英文别名: Bn(-3)[Bn(-4)][Mes(-6)]Glc2Ac(b)-SPh；[(2S,3R,4S,5R,6R)-6-(methylsulfonyloxymethyl)-4,5-bis(phenylmethoxy)-2-phenylsulfanyloxan-3-yl] acetate
• CAS: 261926-70-9
• 化学式: C₂₉H₃₂O₈S₂
• 分子量: 572.7
• InChiKey: SQNUJTZOILLBHG-RQKPWJHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-acetyl-3,4-di-O-benzyl-6-O-mesyl-1-thio-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 氢氧化钾 、 sodium tetrahydroborate 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 Angstroem MS 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.0h， 生成 (1R,3S,5R,6R,7S,8R,20S,22R,24R,25R,26S,27R,29S,31R,32R,33R)-33-hydroxy-5,24,31-trimethyl-6,25,26,32-tetrakis(phenylmethoxy)-7-prop-2-enoxy-20-propyl-2,4,9,21,23,28,30-heptaoxatetracyclo[27.3.1.03,8.022,27]tritriacontan-10-one
  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 3,4-di-O-benzyl-1-thio-β-D-glucopyranoside 生成 phenyl 2-O-acetyl-3,4-di-O-benzyl-6-O-mesyl-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