2,3-o-isopropyliden-L-gulono-1,4-lactone | 195833-61-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-o-isopropyliden-L-gulono-1,4-lactone
• 英文别名: (3aS,6S,6aS)-6-[(1S)-1,2-dihydroxyethyl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
• CAS: 195833-61-5
• 化学式: C₉H₁₄O₆
• 分子量: 218.207
• InChiKey: SSSBRIPVSPUGBC-AXMZGBSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-o-isopropyliden-L-gulono-1,4-lactone 在 Amberlite 120-(H+) 作用下， 以76%的产率得到L-铝离子-1,4-内酯
  参考文献：
  名称：

  An efficient synthesis of l-allono-1,4-lactone from 2,3:5,6-di-O-isopropylidene-d-mannono-1,4-lactone

  摘要：

  We reported herein an efficient synthesis of L-allono-1,4-lactone from 2,3:5,6-di-O-isopropylidene-D-inannono-1,4-lactone in five steps. The key feature of this method involved a one-pot, 6 double inversion' procedure at the stereocenters of C-4 and C-5 Of D-mannono- 1,4-lactone to afford the target molecule. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.113
• 作为产物：
  描述：

  2,3:5,6-二-O-异亚丙基-D-甘露糖酸-1,4-内酯 在 吡啶 、 咪唑 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成 2,3-o-isopropyliden-L-gulono-1,4-lactone
  参考文献：
  名称：

  An efficient synthesis of l-allono-1,4-lactone from 2,3:5,6-di-O-isopropylidene-d-mannono-1,4-lactone

  摘要：

  We reported herein an efficient synthesis of L-allono-1,4-lactone from 2,3:5,6-di-O-isopropylidene-D-inannono-1,4-lactone in five steps. The key feature of this method involved a one-pot, 6 double inversion' procedure at the stereocenters of C-4 and C-5 Of D-mannono- 1,4-lactone to afford the target molecule. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.113

文献信息

• Highly selective silver(I) oxide mediated monoprotection of symmetrical diols
  作者：Abderrahim Bouzide、Gilles Sauvé

  DOI：10.1016/s0040-4039(97)01328-2

  日期：1997.8

  Treatment of symmetrical diol with Ag2O and alkyl halide gave the monoprotected derivative in good to excellent yield.

  用Ag 2 O和烷基卤处理对称的二醇以良好至优异的产率得到单保护的衍生物。
• Synthesis of 6-amino-6-deoxy-d-gulono-1,6-lactam and l-gulono-1,6-lactam derived from corresponding 5,6-O-sulfinyl hexono-1,4-lactones
  作者：Laurent Gireaud、Ludovic Chaveriat、Imane Stasik、Anne Wadouachi、Daniel Beaupère

  DOI：10.1016/j.tet.2006.05.017

  日期：2006.7

  Syntheses of 6-amino-6-deoxy-2,3-0-isopropylidene-D-gulono- and L-gulono-1,6-lactams 3 and 4 from corresponding glycono-1,4-lactones are described. Activation of the primary hydroxyl group requires 5,6-cyclic sulfite intermediate to obtain 6-azido-6-deoxy derivatives, which are cyclized after reduction. (c) 2006 Elsevier Ltd. All rights reserved.
• An efficient synthesis of l-allono-1,4-lactone from 2,3:5,6-di-O-isopropylidene-d-mannono-1,4-lactone
  作者：Tzenge-Lien Shih、Jui-Huang Tseng

  DOI：10.1016/j.tetlet.2003.12.113

  日期：2004.2

  We reported herein an efficient synthesis of L-allono-1,4-lactone from 2,3:5,6-di-O-isopropylidene-D-inannono-1,4-lactone in five steps. The key feature of this method involved a one-pot, 6 double inversion' procedure at the stereocenters of C-4 and C-5 Of D-mannono- 1,4-lactone to afford the target molecule. (C) 2004 Elsevier Ltd. All rights reserved.