(2S,3S)-3-[(benzyloxy)methyl]-2-methyloxiranyl(trimethyl)silane | 1352405-79-8

• 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: (2S,3S)-3-[(benzyloxy)methyl]-2-methyloxiranyl(trimethyl)silane
• CAS: 1352405-79-8
• 化学式: C₁₄H₂₂O₂Si
• 分子量: 250.413
• InChiKey: RKJYMHWCVXGXAY-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  21.76
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-[(benzyloxy)methyl]-2-methyloxiranyl(trimethyl)silane 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 6.83h， 生成 (2R,3R)-1-(benzyloxy)-3-methyl-4-pentyn-2-ol
  参考文献：
  名称：

  Formal synthesis of (+)-neooxazolomycin via a Stille cross-coupling/deconjugation route

  摘要：

  A formal synthesis of neooxazolomycin is described via the preparation of Kende's key intermediate in a longest linear sequence of 23 steps. This work is founded upon the union of three fragments: Moloney's lactam-derived triflate, a vinyl stannane and a Julia-Kocienski sulfone and encompasses three key steps: (i) a Stille cross-coupling to combine the triflate and vinyl stannane, (ii) a base-promoted enone deconjugation to derive the dihydroxylation precursor and (iii) our previously reported Julia-Kocienski methodology to assemble the pentadienyl amine side chain with the sulfone precursor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.037
• 作为产物：
  描述：

  (2E)-3-(trimethylsilyl)crotyl alcohol 在 叔丁基过氧化氢 、 sodium hydride 作用下， 以 四氢呋喃 、 癸烷 、 mineral oil 为溶剂， 反应 17.0h， 生成 (2S,3S)-3-[(benzyloxy)methyl]-2-methyloxiranyl(trimethyl)silane
  参考文献：
  名称：

  Formal synthesis of (+)-neooxazolomycin via a Stille cross-coupling/deconjugation route

  摘要：

  A formal synthesis of neooxazolomycin is described via the preparation of Kende's key intermediate in a longest linear sequence of 23 steps. This work is founded upon the union of three fragments: Moloney's lactam-derived triflate, a vinyl stannane and a Julia-Kocienski sulfone and encompasses three key steps: (i) a Stille cross-coupling to combine the triflate and vinyl stannane, (ii) a base-promoted enone deconjugation to derive the dihydroxylation precursor and (iii) our previously reported Julia-Kocienski methodology to assemble the pentadienyl amine side chain with the sulfone precursor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.037