4-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)phenol | 217482-84-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)phenol
• 英文别名: [(3S,4S,5R,6S)-4,5-diacetyloxy-6-(4-hydroxyphenyl)thian-3-yl] acetate
• CAS: 217482-84-3
• 化学式: C₁₇H₂₀O₇S
• 分子量: 368.408
• InChiKey: VCCUFAUZZFLIAY-TWMKSMIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)phenol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以26%的产率得到4-(5-thio-β-D-xylopyranosyl)phenol
  参考文献：
  名称：

  Synthetic studies in the 5-thio-d-xylopyranose seriespart 3: Preparations ofO-phenyl andC-(4-hydroxyphenyl) 5-thio-d-xylopyranosides

  摘要：

  Treatment of the tri-O-acetyl 5-thio-alpha-xylopyranosyl 1-O-trichloroacetimidate 1 and phenol in the presence of BF3. OEt2 at low temperature led to the corresponding O-phenyl (4: similar to 30 % yield) and C-(4-hydroxyphenyl) 5-thio-D-xylopyranosides (5: similar to 40 % yield) as a result of competitive O-glycosidation and aromatic electrophilic substitution. At higher temperatures, O-phenyl 5-thio-beta-D-xylopyranoside was shown to rearrange readily to give C-(4-hydroxyphenyl) 5-thio-beta-D-xylopylanoside as the thermodynamically favoured product. In the presence of zinc oxide, the sugar alpha-bromide 2 and phenol led also to a mixture of 4 (similar to 20 % yield) and 5 (similar to 40 % yield). Compound 5 was produced from 2 on treatment with dibutyltin diphenoxide and from the 1-O-trimethylsilyl sugar derivative 3 and trimethylsilyloxybenzene, when reacted in the presence of trimethylsilyl triflate in dichloromethane (35 % yield). Under these conditions, a tetrahydrothiophene derivative was observed (6: similar to 5 % yield). However, the sulfur transannular participation pathway which accounted for its formation became predominant when the alpha-bromide 2 and phenol were treated for several hours with zinc chloride, thus affording 6 in a 42 % yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00848-5
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranose 在 三氟甲磺酸三甲基硅酯 、 三乙胺 、 六甲基二硅氮烷 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 4.75h， 生成 4-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)phenol
  参考文献：
  名称：

  Synthetic studies in the 5-thio-d-xylopyranose seriespart 3: Preparations ofO-phenyl andC-(4-hydroxyphenyl) 5-thio-d-xylopyranosides

  摘要：

  Treatment of the tri-O-acetyl 5-thio-alpha-xylopyranosyl 1-O-trichloroacetimidate 1 and phenol in the presence of BF3. OEt2 at low temperature led to the corresponding O-phenyl (4: similar to 30 % yield) and C-(4-hydroxyphenyl) 5-thio-D-xylopyranosides (5: similar to 40 % yield) as a result of competitive O-glycosidation and aromatic electrophilic substitution. At higher temperatures, O-phenyl 5-thio-beta-D-xylopyranoside was shown to rearrange readily to give C-(4-hydroxyphenyl) 5-thio-beta-D-xylopylanoside as the thermodynamically favoured product. In the presence of zinc oxide, the sugar alpha-bromide 2 and phenol led also to a mixture of 4 (similar to 20 % yield) and 5 (similar to 40 % yield). Compound 5 was produced from 2 on treatment with dibutyltin diphenoxide and from the 1-O-trimethylsilyl sugar derivative 3 and trimethylsilyloxybenzene, when reacted in the presence of trimethylsilyl triflate in dichloromethane (35 % yield). Under these conditions, a tetrahydrothiophene derivative was observed (6: similar to 5 % yield). However, the sulfur transannular participation pathway which accounted for its formation became predominant when the alpha-bromide 2 and phenol were treated for several hours with zinc chloride, thus affording 6 in a 42 % yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00848-5