1,2,3-Trimethoxy-4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)benzene | 132817-37-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,3-Trimethoxy-4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)benzene
• 英文别名: (2R,3R,4R,5S,6S)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2,3,4-trimethoxyphenyl)oxane
• CAS: 132817-37-9
• 化学式: C₄₃H₄₆O₈
• 分子量: 690.833
• InChiKey: HKFYUHMWZRTOCD-HGQWKZBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.13
• 重原子数：
  51.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  73.84
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1,2,3-Trimethoxy-4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)benzene 在 aluminum (III) chloride 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 异丙基氯化镁 、 sodium hexamethyldisilazane 、 sodium iodide 作用下， 以 四氢呋喃 、 氯仿 、 环己烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 21.25h， 生成 2-(benzyloxy)-3,4-dimethoxy-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)benzaldehyde
  参考文献：
  名称：

  Synthesis of 3,3′-Di-O-methyl Ardimerin and Exploration of Its DNA Binding Properties

  摘要：

  The 3,3'-di-O-methyl derivative (15) of the bis-C-aryl glycoside natural product ardimerin (1) has been synthesized in 11 steps from 2,3,4,6-tetrabenzylglucose (2) and 1,2,3-trimethoxybenzene (3). Key steps in the synthesis involve a Lewis acid mediated Friedel-Crafts type glycosylation and a Yamaguchi lactonization under Yonemitsu conditions. 3,3'-Di-O-methyl ardimerin aggregates in aqueous solutions at concentrations greater than 1 mu M, and both UV and fluorescence binding studies indicate that 15 has a low affinity for duplex DNA.

  DOI：

  10.1021/ol500725e
• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1,2,3-Trimethoxy-4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)benzene
  参考文献：
  名称：

  Synthesis of 3,3′-Di-O-methyl Ardimerin and Exploration of Its DNA Binding Properties

  摘要：

  The 3,3'-di-O-methyl derivative (15) of the bis-C-aryl glycoside natural product ardimerin (1) has been synthesized in 11 steps from 2,3,4,6-tetrabenzylglucose (2) and 1,2,3-trimethoxybenzene (3). Key steps in the synthesis involve a Lewis acid mediated Friedel-Crafts type glycosylation and a Yamaguchi lactonization under Yonemitsu conditions. 3,3'-Di-O-methyl ardimerin aggregates in aqueous solutions at concentrations greater than 1 mu M, and both UV and fluorescence binding studies indicate that 15 has a low affinity for duplex DNA.

  DOI：

  10.1021/ol500725e

文献信息

• Synthesis of bergenin-type C-glucosylarenes
  作者：Wendelin Frick、Richard R. Schmidt

  DOI：10.1016/0008-6215(91)80148-g

  日期：1991.1

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

  DOI：——

  日期：——