Acetic acid (1S,2S)-2-acetoxy-1-[(4R,5R)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-bromo-propyl ester | 138638-14-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (1S,2S)-2-acetoxy-1-[(4R,5R)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-bromo-propyl ester
• CAS: 138638-14-9
• 化学式: C₂₀H₂₆BrNO₇
• 分子量: 472.333
• InChiKey: GAJUALZKRAPAEP-NCXUSEDFSA-N

反应信息

• 作为反应物：
  描述：

  Acetic acid (1S,2S)-2-acetoxy-1-[(4R,5R)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-bromo-propyl ester 在 偶氮二异丁腈 (n-Bu)3Sn 作用下， 以 苯 为溶剂， 生成 Acetic acid (3aR,4R,5R,7R,7aR)-5-acetoxy-7-benzyloxyamino-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester 、 Acetic acid (3aR,4R,5R,7S,7aR)-5-acetoxy-7-benzyloxyamino-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester
  参考文献：
  名称：

  Carbocycles from carbohydrates: a free radical route to aminocyclitol derivatives

  摘要：

  Some derivatives of (1R,2R,3R,4S,5R) and (1R,2R,3R,4R,5S)-5-amino-1,2,3,4-cyclohexanetetrol have been synthesized from acyclic carbohydrate intermediates via 6-exo free radical cyclization.

  DOI：

  10.1016/0040-4039(91)80189-d
• 作为产物：
  描述：

  苄氧基胺盐酸盐 在 吡啶 、 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 42.0h， 生成 Acetic acid (1S,2S)-2-acetoxy-1-[(4R,5R)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-bromo-propyl ester
  参考文献：
  名称：

  6-Exo free radical cyclization of acyclic carbohydrate intermediates: a new synthetic route to enantiomerically pure polyhydroxylated cyclohexane derivatives

  摘要：

  The 6-exo free radical cyclization of conveniently functionalized acyclic carbohydrate derivatives is a new and efficient method for the asymmetric synthesis of polyhydroxylated cyclohexane compounds (aminocyclitols, pseudosugars). The scope and versatility of this synthetic route has been analyzed by changing the absolute configuration of the radical precursors and the nature of the radical trap. The yield and stereoselectivity in this process is very structure dependent.

  DOI：

  10.1021/jo00035a017