(2S,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine | 1570183-94-6

• 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,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine
• 英文别名: β-C-allyl-2,3,4,6-tetra-O-benzyl-1-deoxynojirimycin；(3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine
• CAS: 1570183-94-6
• 化学式: C₃₇H₄₁NO₄
• 分子量: 563.737
• InChiKey: FUUDCJQRROFRFU-HKPHLGJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.88
• 重原子数：
  42.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  48.95
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine 在 三氟甲磺酸三甲基硅酯 、 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 反应 0.08h， 生成
  参考文献：
  名称：

  Site-Selective Debenzylation of C-Allyl Iminosugars Enables Their Stereocontroled Structure Diversification at the C-2 Position

  摘要：

  A C-2 regioselective debenzylative cycloetherification/reductive elimination sequence applied to perbenzylated C-allyl iminosugars is described. This NIS/TMSOTf-triggered deprotection was successfully applied to five-, six-, and seven-membered C-allyl iminosugars including 1,2 cis and 1,2 trans stereoisomers. It allows rapid introduction of structural diversity at the key C-2 position in a stereoselective manner exploiting the anchimeric assistance of the intracyclic N-benzyl group, giving access to the 2-acetamido and 2-fluoro d-gluco configured C-allyl iminosugars and to the epimeric d-manno derivative.

  DOI：

  10.1021/acs.orglett.9b01712
• 作为产物：
  描述：

  (2R,3R,4R,5S,6S)-N-benzyl-3,4,5-tris(benzyloxy)-2-benzyloxymethyl-6-(prop-2-enyl)piperidine 在 ammonium cerium (IV) nitrate 作用下， 以 四氢呋喃 、 水 为溶剂， 以73%的产率得到(2S,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine
  参考文献：
  名称：

  Site-Selective Debenzylation of C-Allyl Iminosugars Enables Their Stereocontroled Structure Diversification at the C-2 Position

  摘要：

  A C-2 regioselective debenzylative cycloetherification/reductive elimination sequence applied to perbenzylated C-allyl iminosugars is described. This NIS/TMSOTf-triggered deprotection was successfully applied to five-, six-, and seven-membered C-allyl iminosugars including 1,2 cis and 1,2 trans stereoisomers. It allows rapid introduction of structural diversity at the key C-2 position in a stereoselective manner exploiting the anchimeric assistance of the intracyclic N-benzyl group, giving access to the 2-acetamido and 2-fluoro d-gluco configured C-allyl iminosugars and to the epimeric d-manno derivative.

  DOI：

  10.1021/acs.orglett.9b01712

文献信息

• Concise synthesis of bicyclic iminosugars <i>via</i> reductive functionalization of sugar-derived lactams and subsequent RCM reaction
  作者：Piotr Szcześniak、Bartłomiej Furman

  DOI：10.1039/d1ob01172c

  日期：——

  method for the synthesis of bicyclic iminosugars has been developed. The strategy is based on the partial reduction of sugar-derived lactams by Schwartz's reagent and tandem stereoselective nucleophile addition dictated by Woerpel's model which affords polyhydroxylated cyclic amines as key intermediates. Introduction of a vinyl or allyl group to the iminosugar produces diene derivatives that can be

  开发了一种合成双环亚氨基糖的有效方法。该策略基于通过 Schwartz 试剂和串联立体选择性亲核试剂加成的糖衍生内酰胺的部分还原，由 Woerpel 模型提供多羟基化环胺作为关键中间体。将乙烯基或烯丙基基团引入亚氨基糖产生二烯衍生物，该衍生物可以进行闭环复分解反应 (RCM)，以良好至极好的产率提供多羟基化吡咯里西啶、中氮茚和喹唑啉衍生物。该反应序列已应用于风信子 A 2的正式合成，它是一种多羟基化的吡咯里西啶生物碱。
• Sugar-derived cyclic imines: one-pot synthesis and direct functionalization
  作者：Piotr Szcześniak、Sebastian Stecko、Olga Staszewska-Krajewska、Bartłomiej Furman

  DOI：10.1016/j.tet.2014.01.039

  日期：2014.3

  A simple method for the synthesis of sugar-derived imines by a Schwartz's reagent reduction of easily available sugar lactams has been described. A direct addition of nucleophiles to the generated in situ cyclic imines and subsequent deprotection of hydroxyl function allows to convert sugar lactams in polyhydroxylated pyrrolidines and piperidines. (C) 2014 Elsevier Ltd. All rights