(2R,3R)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methyl-6-phenylsulfanyl-3,4-dihydro-2H-pyran | 936016-72-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2R,3R)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methyl-6-phenylsulfanyl-3,4-dihydro-2H-pyran
• CAS: 936016-72-7
• 化学式: C₁₇H₂₂O₃S
• 分子量: 306.426
• InChiKey: SYKOKLPCVMDVAR-XNRPHZJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  53
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methyl-6-phenylsulfanyl-3,4-dihydro-2H-pyran 、 (3S,5S)-5-[tert-butyl(dimethyl)silyl]oxydec-9-ene-1,3-diol 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以86%的产率得到tert-butyl-[(2S)-1-[(4S,6R,8R,9R)-8-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-9-methyl-1,5,7-trioxaspiro[5.5]undecan-4-yl]hept-6-en-2-yl]oxy-dimethylsilane
  参考文献：
  名称：

  A Reductive Cyclization Approach to Attenol A

  摘要：

  A reductive cyclization strategy was applied to the synthesis of attenol A. This nontraditional approach to the spiroacetal structure illustrated several advantages of the reductive cyclization methodology. The attenol A core was formed in a carbon-carbon bond coupling that gave rise to a previously inaccessible spiroacetal epimer, a new method to synthesize thioketene acetals from a phenyl sulfone was realized, and the configurational stability of a nonanomeric spiroacetal was evaluated. A minor byproduct in the reductive cyclization reaction was identified that for the first time allowed direct evaluation of the stereoselectivity in a reductive cyclization of a dialkyloxy alkyllithium reagent.

  DOI：

  10.1021/jo0626459
• 作为产物：
  描述：

  (1R,2R)-2-methyl-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 4-二甲氨基吡啶 、 N-苯基双(三氟甲烷磺酰)亚胺 、 双(三甲基硅烷基)氨基钾 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， -78.0~20.0 ℃ 、689.47 kPa 条件下， 反应 26.75h， 生成 (2R,3R)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methyl-6-phenylsulfanyl-3,4-dihydro-2H-pyran
  参考文献：
  名称：

  A Reductive Cyclization Approach to Attenol A

  摘要：

  A reductive cyclization strategy was applied to the synthesis of attenol A. This nontraditional approach to the spiroacetal structure illustrated several advantages of the reductive cyclization methodology. The attenol A core was formed in a carbon-carbon bond coupling that gave rise to a previously inaccessible spiroacetal epimer, a new method to synthesize thioketene acetals from a phenyl sulfone was realized, and the configurational stability of a nonanomeric spiroacetal was evaluated. A minor byproduct in the reductive cyclization reaction was identified that for the first time allowed direct evaluation of the stereoselectivity in a reductive cyclization of a dialkyloxy alkyllithium reagent.

  DOI：

  10.1021/jo0626459

文献信息

• A Reductive Cyclization Approach to Attenol A
  作者：Thomas E. La Cruz、Scott D. Rychnovsky

  DOI：10.1021/jo0626459

  日期：2007.3.1

  A reductive cyclization strategy was applied to the synthesis of attenol A. This nontraditional approach to the spiroacetal structure illustrated several advantages of the reductive cyclization methodology. The attenol A core was formed in a carbon-carbon bond coupling that gave rise to a previously inaccessible spiroacetal epimer, a new method to synthesize thioketene acetals from a phenyl sulfone was realized, and the configurational stability of a nonanomeric spiroacetal was evaluated. A minor byproduct in the reductive cyclization reaction was identified that for the first time allowed direct evaluation of the stereoselectivity in a reductive cyclization of a dialkyloxy alkyllithium reagent.