tetra-O-benzyl-β-D-glucopyranosyl trifluoroacetate | 129889-18-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tetra-O-benzyl-β-D-glucopyranosyl trifluoroacetate
• 英文别名: 2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl trifluoroacetate；[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] 2,2,2-trifluoroacetate
• CAS: 129889-18-5
• 化学式: C₃₆H₃₅F₃O₇
• 分子量: 636.665
• InChiKey: DHUANDIOYIPWEP-RUOAZZEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.79
• 重原子数：
  46.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  tetra-O-benzyl-β-D-glucopyranosyl trifluoroacetate 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 正丁基锂 、 三氟化硼乙醚 、 氢气 、 溴 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 溶剂黄146 为溶剂， 反应 34.33h， 生成 2,3,4-Trimethoxy-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-benzoic acid methyl ester
  参考文献：
  名称：

  Synthesis of bergenin-type C-glucosylarenes

  摘要：

  Reaction of 1,2,3-trimethoxybenzene with 2,3,4,6-tetra-O-benzyl-beta-d-glucopyranosyl trifluoroacetate (5) in the presence of BF3.OEt2 afforded the 4-beta-C-glycosylarene 6. Hydrogenolysis of 6, then O-methoxycarbonylation, and bromination gave 1-bromo-2,3,4-trimethoxy-5-(2,3,4,6-tetra-O-methoxycarbonyl-beta-d-glucopyranosyl)benzene (9). Bromine/lithium exchange of 9 and then reaction with diphenyl disulfide furnished 2,3,4-trimethoxy-1-phenylthio-5-(2,3,4,6-tetra-O-methoxycarbonyl-beta-D-glucopyranosyl)benzene (14), oxidation of which afforded the phenylsulfinyl derivative 15. Ortho-lithiaton of 15 and then reaction with methyl chloroformate gave 2,3,4-trimethoxy-6-methoxycarbonyl-1-phenylsulfinyl-5-(2,3,4,6-tetra-O-methoxycarbonyl-beta-D-glucop? yranosyl)benzene (17). Removal of the phenylsulfinyl group from 15 with Raney nickel and then lactonisation with sodium methoxide provided 8,10-di-O-methylbergenin (2). The 3,4,11-triacette (4) of 2 had physical data that accorded with those for the natural compound.

  DOI：

  10.1016/0008-6215(91)80148-g
• 作为产物：
  描述：

  2,3,4,6-O-四苄基-α-D-葡萄糖 、 三氟乙酸酐 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 tetra-O-benzyl-β-D-glucopyranosyl trifluoroacetate
  参考文献：
  名称：

  Synthesis of bergenin-type C-glucosylarenes

  摘要：

  Reaction of 1,2,3-trimethoxybenzene with 2,3,4,6-tetra-O-benzyl-beta-d-glucopyranosyl trifluoroacetate (5) in the presence of BF3.OEt2 afforded the 4-beta-C-glycosylarene 6. Hydrogenolysis of 6, then O-methoxycarbonylation, and bromination gave 1-bromo-2,3,4-trimethoxy-5-(2,3,4,6-tetra-O-methoxycarbonyl-beta-d-glucopyranosyl)benzene (9). Bromine/lithium exchange of 9 and then reaction with diphenyl disulfide furnished 2,3,4-trimethoxy-1-phenylthio-5-(2,3,4,6-tetra-O-methoxycarbonyl-beta-D-glucopyranosyl)benzene (14), oxidation of which afforded the phenylsulfinyl derivative 15. Ortho-lithiaton of 15 and then reaction with methyl chloroformate gave 2,3,4-trimethoxy-6-methoxycarbonyl-1-phenylsulfinyl-5-(2,3,4,6-tetra-O-methoxycarbonyl-beta-D-glucop? yranosyl)benzene (17). Removal of the phenylsulfinyl group from 15 with Raney nickel and then lactonisation with sodium methoxide provided 8,10-di-O-methylbergenin (2). The 3,4,11-triacette (4) of 2 had physical data that accorded with those for the natural compound.

  DOI：

  10.1016/0008-6215(91)80148-g

文献信息

• The first direct method for C-glucopyranosyl derivatization of 2,3,4,6-tetra-O-benzyl-D-glucopyranose
  作者：Pietro Allevi、Mario Anastasia、Pierangela Ciuffreda、Alberto Fiecchi、Antonio Scala

  DOI：10.1039/c39870001245

  日期：——

  Commercially available 2,3,4,6-tetra-O-benzyl-D-glucopyranose, activated by trifluoroacetic anhydride reacts, in the presence of Lewis acids, with various silyl enol ethers or with allylsilane to yield C-D-glucopyranosyl derivatives of the α-configuration, and with activated aromatic nucleophiles to yield the corresponding β-anomers.

  在路易斯酸存在下，由三氟乙酸酐活化的可商购获得的2,3,4,6-四-O-苄基-D-吡喃吡喃糖与各种甲硅烷基烯醇醚或烯丙基硅烷反应生成C - D-吡喃葡糖基衍生物α-构型，并带有活化的芳族亲核试剂，可产生相应的β-异头物。
• The first total synthesis of carminic acid
  作者：Pietro Allevi、Mario Anastasia、Pierangela Ciuffreda、Alberto Fiecchi、Antonio Scala、Steve Bingham、Max Muir、John Tyman

  DOI：10.1039/c39910001319

  日期：——

  The first synthesis of carminic acid (7β-D-glucopyranosyl-1-methyl-3,5,6,8-tetrahydroxy-9,10-anthraquinone-2-carboxylic acid), was accomplished by direct C-glucosylation of ethyl 3,5,8,9,10-pentamethoxy-1-methylanthracene-2-carboxylate, here synthesized, which affords ethyl 7-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3,5,8,9,10-pentamethoxy-1-methylanthracene-2-carboxylate and carminic acid by regeneration of the masked functionalities.

  胭脂红酸（7β-D-吡喃葡萄糖基-1-甲基-3,5,6,8-四羟基-9,10-蒽醌-2-羧酸）的首次合成是通过乙基3的直接C-葡萄糖基化完成的，此处合成的5,8,9,10-五甲氧基-1-甲基蒽-2-甲酸酯，其提供乙基7-(2,3,4,6-四-O-苄基-β-D-吡喃葡萄糖基)-3，通过掩蔽官能团的再生得到5,8,9,10-五甲氧基-1-甲基蒽-2-羧酸酯和胭脂红酸。
• Allevi, Pietro; Anastasia, Mario; Ciuffreda, Pierangela, Journal of the Chemical Society. Perkin transactions I, 1989, p. 1275 - 1280
  作者：Allevi, Pietro、Anastasia, Mario、Ciuffreda, Pierangela、Fiecchi, Alberto、Scala, Antonio

  DOI：——

  日期：——