1,1²-anhydro-1-C-<2-(hydroxymethyl)-4,6-dimethoxyphenyl>-β-D-glucopyranose tetraacetate | 76843-40-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1,1²-anhydro-1-C-<2-(hydroxymethyl)-4,6-dimethoxyphenyl>-β-D-glucopyranose tetraacetate
• 英文别名: 1,1-anhydro-1-C-<6-(hydroxymethyl)-2,4-dimethoxyphenyl>-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose；1,1-anhydro-1-C-<2-(hydroxymethyl)4,6-dimethoxyphenyl>-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose；1,1²-anhydro-1-C-[2-(hydroxymethyl)-4,6-dimethoxyphenyl]-β-D-glucopyranose tetraacetate；[(2'R,3S,3'R,4'S,5'R)-3',4',5'-triacetyloxy-4,6-dimethoxyspiro[1H-2-benzofuran-3,6'-oxane]-2'-yl]methyl acetate
• CAS: 76843-40-8
• 化学式: C₂₃H₂₈O₁₂
• 分子量: 496.468
• InChiKey: QPWSWHKQUUHCNR-IFPLKCGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  5-内酯 在 palladium on activated charcoal 吡啶 、 三乙基硅烷 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 、 甲苯 、 Petroleum ether 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 生成 1,1²-anhydro-1-C-<2-(hydroxymethyl)-4,6-dimethoxyphenyl>-β-D-glucopyranose tetraacetate
  参考文献：
  名称：

  C-Glycosides. 9. Stereospecific synthesis of C-glycosidic spiroketal of the papulacandins

  摘要：

  The reaction of ortho-lithiated triphenylmethyl benzyl ether with perbenzylated D-gluconolactone 1 followed by cyclization by BF3.Et2O provides a new stereospecific synthesis of C-glycosidic spiroketals. The structure of the peracetylated derivative was determined by X-ray diffraction. This methodology is applied to the synthesis of the spiroketal unit of papulacandins.

  DOI：

  10.1021/jo00022a014

文献信息

• Total Synthesis and Structural Elucidation of the Antifungal Agent Papulacandin D
  作者：Anthony G. M. Barrett、Michael Peña、J. Adam Willardsen

  DOI：10.1021/jo951895e

  日期：1996.1.1

  Condensation of the aryllithium reagents, prepared from the bromides 10 and 11 and tert-butyllithium, with lactone 19 and acid-catalyzed spirocyclization gave the papulacandin spiroketals 14 and 15. Subsequent protection using di-tert-butylsilyl bis(trifluoromethanesulfonate) gave the diols 31 and 30. Isoleucine (37) was converted using a double Wittig reaction sequence and propargylation of the intermediate aldehyde 46 into the alkynol 47. Separation of the C-7 epimers of 47 was achieved using kinetic resolution via Sharpless epoxidation. Both alkynol epimers 53 and 57 were converted into the papulacandin side chain esters 65 and 66 using a hydrozirconation and palladium(0)-catalyzed coupling sequence. Comparisons of Mosher ester derivatives of 65 and 66 with the Mosher ester derivative of the natural papulacandin side chain and further degradation were consistent with the stereochemistry of the natural product being 7S,14S. Esterification of the spiroketals with the mixed anhydride 70 and global deprotection gave papulacandin D (1).
• Short synthesis of c-aryl-glucopyranosides of the papulacandin type
  作者：Richard R. Schmidt(rk)、Wendelin Frick

  DOI：10.1016/s0040-4020(01)86084-1

  日期：1988.1