1-Benzenesulfonyl-2-[(3aS,4S,6R,6aR)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-1H-indole | 927677-25-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-Benzenesulfonyl-2-[(3aS,4S,6R,6aR)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-1H-indole
• CAS: 927677-25-6
• 化学式: C₃₈H₄₁NO₆SSi
• 分子量: 667.898
• InChiKey: OREFLCRGHBTBBX-UDCWBUBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.41
• 重原子数：
  47.0
• 可旋转键数：
  8.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  75.99
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-Benzenesulfonyl-2-[(3aS,4S,6R,6aR)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-1H-indole 在 四丁基氟化铵 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 生成 (2S,3R,4S,5R)-2-(1-Benzenesulfonyl-1H-indol-2-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol
  参考文献：
  名称：

  Efficient Stereoselective Synthesis of New C-Nucleosides via Intramolecular Mitsunobu Cyclization

  摘要：

  We have studied the stereoselective synthesis of new C-nucleosides by heteroarylation of the protected gamma-ribonolactone by means of heteroaromatic systems such as indole, thiazoles, imidazoles and benzimidazoles. We have observed that the first anion addition-limiting step is very sensitive to steric factors induced by the N-protective groups in a-position.

  DOI：

  10.1080/15257779908041510
• 作为产物：
  描述：

  5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone 在 sodium tetrahydroborate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1-Benzenesulfonyl-2-[(3aS,4S,6R,6aR)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-1H-indole
  参考文献：
  名称：

  Efficient Stereoselective Synthesis of New C-Nucleosides via Intramolecular Mitsunobu Cyclization

  摘要：

  We have studied the stereoselective synthesis of new C-nucleosides by heteroarylation of the protected gamma-ribonolactone by means of heteroaromatic systems such as indole, thiazoles, imidazoles and benzimidazoles. We have observed that the first anion addition-limiting step is very sensitive to steric factors induced by the N-protective groups in a-position.

  DOI：

  10.1080/15257779908041510