methyl (3S,7aS)-3-tert-butyl-7-hydroxy-6-methyl-5-oxo-1,3-dihydropyrrolo[1,2-c][1,3]oxazole-7a-carboxylate | 1352405-72-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (3S,7aS)-3-tert-butyl-7-hydroxy-6-methyl-5-oxo-1,3-dihydropyrrolo[1,2-c][1,3]oxazole-7a-carboxylate
• CAS: 1352405-72-1
• 化学式: C₁₃H₁₉NO₅
• 分子量: 269.298
• InChiKey: KATOFSQFUYEKFD-GWCFXTLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (3S,7aS)-3-tert-butyl-7-hydroxy-6-methyl-5-oxo-1,3-dihydropyrrolo[1,2-c][1,3]oxazole-7a-carboxylate 在 2,6-二甲基吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三(2-呋喃基)膦 、 sodium acetate 、 N,N-二异丙基乙胺 、 对甲苯磺酰肼 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.25h， 生成 (3S,7aR)-methyl 7-((3R,4R)-5-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-methylpentyl)-3-tert-butyl-6-methyl-5-oxo-1,3,5,7a-tetrahydropyrrolo[1,2-c]oxazole-7a-carboxylate
  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：

  methyl (R)-2-tert-butyloxazolidine-4-carboxylate 在 吡啶 、 potassium tert-butylate 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 生成 methyl (3S,7aS)-3-tert-butyl-7-hydroxy-6-methyl-5-oxo-1,3-dihydropyrrolo[1,2-c][1,3]oxazole-7a-carboxylate
  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

文献信息

• Formal synthesis of (+)-neooxazolomycin via a Stille cross-coupling/deconjugation route
  作者：Reyhan Bastin、James W. Dale、Michael G. Edwards、Julien P.N. Papillon、Michael R. Webb、Richard J.K. Taylor

  DOI：10.1016/j.tet.2011.09.037

  日期：2011.12

  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.