2,3,4-Trimethoxy-1-phenylthio-5-(2,3,4,6-tetra-O-methoxycarbonyl-β-D-glucopyranosyl)benzene | 132817-44-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-Trimethoxy-1-phenylthio-5-(2,3,4,6-tetra-O-methoxycarbonyl-β-D-glucopyranosyl)benzene
• 英文别名: [(2R,3R,4R,5S,6S)-3,5-bis(methoxycarbonyloxy)-2-(methoxycarbonyloxymethyl)-6-(2,3,4-trimethoxy-5-phenylsulfanylphenyl)oxan-4-yl] methyl carbonate
• CAS: 132817-44-8
• 化学式: C₂₉H₃₄O₁₆S
• 分子量: 670.645
• InChiKey: BOAYTZYOGMTQKF-YPPFQWBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  46.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  179.04
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  2,3,4-Trimethoxy-1-phenylthio-5-(2,3,4,6-tetra-O-methoxycarbonyl-β-D-glucopyranosyl)benzene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以83%的产率得到2,3,4-Trimethoxy-1-phenylsulfinyl-5-(2,3,4,6-tetra-O-methoxycarbonyl-β-D-glucopyranosyl)benzene
  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：

  1,2,3-三甲氧基苯 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 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 溶剂黄146 为溶剂， 反应 12.83h， 生成 2,3,4-Trimethoxy-1-phenylthio-5-(2,3,4,6-tetra-O-methoxycarbonyl-β-D-glucopyranosyl)benzene
  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

• FRICK, WENDELIN;SCHMIDT, RICHARD R., CARBOHYDR. RES., 209,(1991) C. 101-107
  作者：FRICK, WENDELIN、SCHMIDT, RICHARD R.

  DOI：——

  日期：——