(2S,3S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-nitro-butyric acid methyl ester | 467425-65-6

• 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)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-nitro-butyric acid methyl ester
• CAS: 467425-65-6
• 化学式: C₁₇H₂₃NO₆
• 分子量: 337.373
• InChiKey: YIMMOBVRODLRAU-RRFJBIMHSA-N

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-nitro-butyric acid methyl ester 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以100%的产率得到(3S,4S,5S)-3-benzyl-5-hydroxymethyl-4-nitromethyldihydrofuran-2-one
  参考文献：
  名称：

  Selective conjugate addition of nitromethane to enoates derived from d-mannitol and l-tartaric acid

  摘要：

  The conjugate addition of nitromethane to enoates prepared from D-(+)-mannitol, substituted at the alpha-position by a methyl or a benzyl group, was investigated. While excellent syn-selectivity (d.e. >90%) was obtained from a-benzyl enoates (used as a mixture of epimers, E/Z=1.8:1), for alpha-methyl enoates the selectivity depended on the stereochemistry of the double bond in the acceptor (d.e. >90% for the (Z)-enoate and 50% for the (E)-enoate). In all cases, a mixture of epimers was formed at the newly generated stereocenter at the a-position. The epimeric syn-adducts were transformed into the corresponding pure alpha,beta,gamma-trisubstituted gamma-butyrolactones by cyclization in acid medium followed by epimerization of the stereocenter at the a-position in DBU/CH2Cl2. When enoates derived from L-tartaric acid were used as acceptors, syn-selective conjugate additions were also observed (d.e. >90% for the (Z)-isomer and 50% for the (E)-isomer). The configuration at the newly generated stereogenic centers were assigned based on X-ray analyses, H-1-H-1 coupling constants and NOE experiments in NMR spectroscopy. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00230-6
• 作为产物：
  描述：

  硝基甲烷 、 methyl (4S)-2-benzyl-4,5-isopropylidenedioxy-2-pentenoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 96.0h， 生成 (2R,3S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-nitro-butyric acid methyl ester 、 (2S,3S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-nitro-butyric acid methyl ester
  参考文献：
  名称：

  Selective conjugate addition of nitromethane to enoates derived from d-mannitol and l-tartaric acid

  摘要：

  The conjugate addition of nitromethane to enoates prepared from D-(+)-mannitol, substituted at the alpha-position by a methyl or a benzyl group, was investigated. While excellent syn-selectivity (d.e. >90%) was obtained from a-benzyl enoates (used as a mixture of epimers, E/Z=1.8:1), for alpha-methyl enoates the selectivity depended on the stereochemistry of the double bond in the acceptor (d.e. >90% for the (Z)-enoate and 50% for the (E)-enoate). In all cases, a mixture of epimers was formed at the newly generated stereocenter at the a-position. The epimeric syn-adducts were transformed into the corresponding pure alpha,beta,gamma-trisubstituted gamma-butyrolactones by cyclization in acid medium followed by epimerization of the stereocenter at the a-position in DBU/CH2Cl2. When enoates derived from L-tartaric acid were used as acceptors, syn-selective conjugate additions were also observed (d.e. >90% for the (Z)-isomer and 50% for the (E)-isomer). The configuration at the newly generated stereogenic centers were assigned based on X-ray analyses, H-1-H-1 coupling constants and NOE experiments in NMR spectroscopy. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00230-6