O-benzyl furanodictine A | 677334-87-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-benzyl furanodictine A
• 英文别名: [(3R,3aS,6R,6aR)-6-acetamido-5-phenylmethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 3-methylbutanoate
• CAS: 677334-87-1
• 化学式: C₂₀H₂₇NO₆
• 分子量: 377.437
• InChiKey: RGVPSKGVRFWQEZ-LSLCXQBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O-benzyl furanodictine A 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以87%的产率得到2-acetamido-3,6-anhydro-2-deoxy-5-O-isovaleryl-D-glucofuranose
  参考文献：
  名称：

  Novel and stereoselective asymmetric synthesis of an amino sugar analogue, furanodictine A

  摘要：

  A novel and efficient strategy is described for the asymmetric synthesis of the first 3,6-anhydrosugar to be isolated from natural sources, furanodictine A. The synthetic process is based on requisite stereodefined manipulation of the functionalized amino alcohol obtained through nucleophilic addition of vinyl Grignard reagent to the aminal incorporating the D-arabinofuranosederived skeleton in a complete stereoselective manner. (C)( 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.135
• 作为产物：
  描述：

  N-(4-Methoxy-benzyl)-N-((1S,2R,3R,4R)-2,3,5-tris-benzyloxy-4-hydroxy-1-vinyl-pentyl)-acetamide 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 sodium periodate 、 四氧化锇 、 N-甲基吲哚酮 、 ammonium cerium(IV) nitrate 、 氢气 、 二正丁基氧化锡 、 potassium carbonate 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 silver(l) oxide 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 乙酸乙酯 、 丙酮 为溶剂， 生成 O-benzyl furanodictine A
  参考文献：
  名称：

  Novel and stereoselective asymmetric synthesis of an amino sugar analogue, furanodictine A

  摘要：

  A novel and efficient strategy is described for the asymmetric synthesis of the first 3,6-anhydrosugar to be isolated from natural sources, furanodictine A. The synthetic process is based on requisite stereodefined manipulation of the functionalized amino alcohol obtained through nucleophilic addition of vinyl Grignard reagent to the aminal incorporating the D-arabinofuranosederived skeleton in a complete stereoselective manner. (C)( 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.135

文献信息

• Novel and stereoselective asymmetric synthesis of an amino sugar analogue, furanodictine A
  作者：Hidemi Yoda、Yuji Suzuki、Kunihiko Takabe

  DOI：10.1016/j.tetlet.2003.12.135

  日期：2004.2

  A novel and efficient strategy is described for the asymmetric synthesis of the first 3,6-anhydrosugar to be isolated from natural sources, furanodictine A. The synthetic process is based on requisite stereodefined manipulation of the functionalized amino alcohol obtained through nucleophilic addition of vinyl Grignard reagent to the aminal incorporating the D-arabinofuranosederived skeleton in a complete stereoselective manner. (C)( 2004 Elsevier Ltd. All rights reserved.