((3R,3aS,4S,6aS)-4-((2R,3R)-3-(ethanoyloxy)-4-hydroxy-2-methylbutyl)-3a-hydroxy-1,3-dimethyl-2,6-dioxohexahydro-1H-furo[3,4-b]pyrrol-6a-yl)methyl ethanoate | 1352406-10-0

• 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: ((3R,3aS,4S,6aS)-4-((2R,3R)-3-(ethanoyloxy)-4-hydroxy-2-methylbutyl)-3a-hydroxy-1,3-dimethyl-2,6-dioxohexahydro-1H-furo[3,4-b]pyrrol-6a-yl)methyl ethanoate
• 英文别名: [(3R,3aS,4S,6aS)-4-[(2R,3R)-3-acetyloxy-4-hydroxy-2-methylbutyl]-3a-hydroxy-1,3-dimethyl-2,6-dioxo-3,4-dihydrofuro[3,4-b]pyrrol-6a-yl]methyl acetate
• CAS: 1352406-10-0
• 化学式: C₁₈H₂₇NO₉
• 分子量: 401.414
• InChiKey: IJRGGZWLBIMBGA-PHQBHPRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ((3R,3aS,4S,6aS)-4-((2R,3R)-3-(ethanoyloxy)-4-hydroxy-2-methylbutyl)-3a-hydroxy-1,3-dimethyl-2,6-dioxohexahydro-1H-furo[3,4-b]pyrrol-6a-yl)methyl ethanoate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以51%的产率得到((3R,3aS,4S,6aS)-4-((2R,3R)-3-(ethanoyloxy)-2-methyl-4-oxobutyl)-3a-hydroxy-1,3-dimethyl-2,6-dioxohexahydro-1H-furo[3,4-b]pyrrol-6a-yl)methyl ethanoate
  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：

  (3R,3aS,4S,6aS)-4-[(2R,3R)-4-(benzyloxy)-3-hydroxy-2-methylbutyl]-3a-hydroxy-6a-(hydroxymethyl)-3-methyldihydro-1H-furo[3,4-b]pyrrole-2,6(3H,4H)-dione 在 吡啶 、 2,6-二甲基吡啶 、 三氟甲磺酸三甲基硅酯 、 20 wt.% Pd(OH)2 on activated carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.5h， 生成 ((3R,3aS,4S,6aS)-4-((2R,3R)-3-(ethanoyloxy)-4-hydroxy-2-methylbutyl)-3a-hydroxy-1,3-dimethyl-2,6-dioxohexahydro-1H-furo[3,4-b]pyrrol-6a-yl)methyl ethanoate
  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