(+/-)-3-(t-butyldimethylsilyloxymethyl)-3,4-dimethyl-pent-4-enoic acid ethyl ester | 681260-77-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+/-)-3-(t-butyldimethylsilyloxymethyl)-3,4-dimethyl-pent-4-enoic acid ethyl ester
• 英文别名: (+)-3-(t-Butyldimethylsilyloxymethyl)-3,4-dimethylpent-4-enoic acid ethyl ester；ethyl 3-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,4-dimethylpent-4-enoate
• CAS: 681260-77-5
• 化学式: C₁₆H₃₂O₃Si
• 分子量: 300.514
• InChiKey: PUBKHQFJYQZVDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-3-(t-butyldimethylsilyloxymethyl)-3,4-dimethyl-pent-4-enoic acid ethyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4 A molecular sieve 、 二异丁基氢化铝 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 9.0h， 生成 (1RS,4SR)-4-(t-butyldimethylsilyloxymethyl)-2,3,4-trimethyl-cyclopent-2-enol
  参考文献：
  名称：

  新型2',3',4'-三甲基支链碳环核苷的合成及抗HCMV活性

  摘要：

  This article reports the synthesis of novel 2',3',4'-trimethyl branched carbocyclic nucleosides. The introduction Of a methyl group in the 2' and 3'-position was accomplished by sequential Horner Wadsworth-Emmons reaction and isopropenyl magnesiumbromide addition, respectively. The construction of the 4'-quaternary carbon needed was carried out using a [3,3]-sigmatropic rearrangement. Bis-vinyls were successfully cyclized using a Grubbs catalyst II. The natural bases (adenine, cytosine) were efficiently coupled with the use of a Pd(0) catalyst.

  DOI：

  10.1081/ncn-200046786
• 作为产物：
  描述：

  (E)-4-(tert-Butyl-dimethyl-silanyloxy)-2,3-dimethyl-but-2-enoic acid ethyl ester 在 二异丁基氢化铝 、 丙酸 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (+/-)-3-(t-butyldimethylsilyloxymethyl)-3,4-dimethyl-pent-4-enoic acid ethyl ester
  参考文献：
  名称：

  新型2',3',4'-三甲基支链碳环核苷的合成及抗HCMV活性

  摘要：

  This article reports the synthesis of novel 2',3',4'-trimethyl branched carbocyclic nucleosides. The introduction Of a methyl group in the 2' and 3'-position was accomplished by sequential Horner Wadsworth-Emmons reaction and isopropenyl magnesiumbromide addition, respectively. The construction of the 4'-quaternary carbon needed was carried out using a [3,3]-sigmatropic rearrangement. Bis-vinyls were successfully cyclized using a Grubbs catalyst II. The natural bases (adenine, cytosine) were efficiently coupled with the use of a Pd(0) catalyst.

  DOI：

  10.1081/ncn-200046786