(S)-2-(tert-butyldiphenylsilyloxy)-1-(furan-2-yl)ethanol | 381164-66-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (S)-2-(tert-butyldiphenylsilyloxy)-1-(furan-2-yl)ethanol
• 英文别名: (1S)-2-[tert-butyl(diphenyl)silyl]oxy-1-(furan-2-yl)ethanol
• CAS: 381164-66-5
• 化学式: C₂₂H₂₆O₃Si
• 分子量: 366.532
• InChiKey: HMAIBIQQGSRNMO-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  42.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-(tert-butyldiphenylsilyloxy)-1-(furan-2-yl)ethanol 在 N-溴代丁二酰亚胺(NBS) 、 sodium acetate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 生成 (S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-hydroxy-6H-pyran-3-one
  参考文献：
  名称：

  Total synthesis and anti-leishmanial activity of R-(−)-argentilactone

  摘要：

  Starting from the commercially available D-glucal (2), the naturally Occurring alpha,beta -unsaturated delta -lactone argentilactone (1a) has been synthesized. The important step is the configuration inversion at C-6 by the Mitsunobu reaction following the sugar-non-sugar-sugar strategy. The synthetic argentilactone has been tested against Leishmania mexicana for bioactivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01559-3
• 作为产物：
  描述：

  D-葡萄烯糖 在 吡啶 、 咪唑 、 甲醇 、 硫酸 、 sodium 、 苯甲酰氯 、 mercury(II) sulfate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (S)-2-(tert-butyldiphenylsilyloxy)-1-(furan-2-yl)ethanol
  参考文献：
  名称：

  Total synthesis and anti-leishmanial activity of R-(−)-argentilactone

  摘要：

  Starting from the commercially available D-glucal (2), the naturally Occurring alpha,beta -unsaturated delta -lactone argentilactone (1a) has been synthesized. The important step is the configuration inversion at C-6 by the Mitsunobu reaction following the sugar-non-sugar-sugar strategy. The synthetic argentilactone has been tested against Leishmania mexicana for bioactivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01559-3

文献信息

• Synthesis of (R)-Dihydropyridones as Key Intermediates for an Efficient Access to Piperidine Alkaloids
  作者：Evangelia Tzanetou、Konstantinos Kasiotis、Prokopios Magiatis、Serkos Haroutounian

  DOI：10.3390/12040735

  日期：——

  transformation of D-glucal to (2R)-hydroxymethyldihydropyridinone 5 in seven steps and 35 % overall yield is reported. Dihydropyridone 5 constitutes a versatile chiral building block for the synthesis of various piperidine alkaloids. In this regard, 5 was converted to piperidinol 13 and piperidinone 15, that may be further elaborated for the syntheses of (+)-desoxoprosophylline (1) and deoxymannojirimycin (3)

  据报道，D-葡糖醛分七步有效转化为 (2R)-羟甲基二氢吡啶酮 5，总产率为 35%。二氢吡啶酮 5 是合成各种哌啶生物碱的通用手性构件。在这方面，5 被转化为哌啶醇 13 和哌啶酮 15，它们可以分别用于 (+)-desoxoprosophylline (1) 和 deoxymannojirimycin (3) 或 D-甘露内酰胺 (4) 的合成。
• Total synthesis and anti-leishmanial activity of R-(−)-argentilactone
  作者：Muhammad Saeed、Thomas Ilg、Miriam Schick、Muhammad Abbas、Wolfgang Voelter

  DOI：10.1016/s0040-4039(01)01559-3

  日期：2001.10

  Starting from the commercially available D-glucal (2), the naturally Occurring alpha,beta -unsaturated delta -lactone argentilactone (1a) has been synthesized. The important step is the configuration inversion at C-6 by the Mitsunobu reaction following the sugar-non-sugar-sugar strategy. The synthetic argentilactone has been tested against Leishmania mexicana for bioactivity. (C) 2001 Elsevier Science Ltd. All rights reserved.