2,3,5-tri-O-benzyl-1-C-propyl-1,4-dideoxy-1,4-imino-L-arabinitol | 1346678-99-6

• 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: 2,3,5-tri-O-benzyl-1-C-propyl-1,4-dideoxy-1,4-imino-L-arabinitol
• 英文别名: (2S,3S,4S,5R)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-5-propylpyrrolidine
• CAS: 1346678-99-6
• 化学式: C₂₉H₃₅NO₃
• 分子量: 445.602
• InChiKey: GYQDQXZOMXTWQX-VVZGZWEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 三氟甲磺酸三甲基硅酯 、 palladium 10% on activated carbon 、 potassium tert-butylate 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醇 、 乙腈 为溶剂， 生成 2,3,5-tri-O-benzyl-1-C-propyl-1,4-dideoxy-1,4-imino-L-arabinitol
  参考文献：
  名称：

  An expeditious synthesis of an analogue of (−)-steviamine by way of the 1,3-dipolar cycloaddition of a nitrile oxide with a 1-C-allyl iminosugar

  摘要：

  In our continuing effort to develop inhibitors of the mycobacterial galactan biosynthesis, we planned to synthesize original iminosugar-based analogues of UDP-galactofuranose by way of the 1,3-dipolar cycloaddition reaction between a 1-C-allyl iminosugar and a nitrile oxide, followed by the reductive cleavage of the resulting isooxazoline. In initial studies, it was found that this last step led in one pot to a new poly-hydroxylated indolizidine derivative closely related to the recently isolated (-)-steviamine, in good yield, by way of a sequence involving at least five individual reactions. The activity of this new compound as a glycosidase inhibitor was evaluated against a panel of glycosidases and compared to (-)-steviamine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.065

文献信息

• En Route to Novel Furanoside Mimics through Stereoselective Zinc-Mediated Propargylation of N-Benzyl Glycofuranosylamines Using Ultrasound Activation
  作者：Olivier Martin、Cyril Nicolas、Francis Engo-Ilanga、Chloé Cocaud

  DOI：10.1055/s-0034-1379551

  日期：——

  Preliminary results on a novel zinc-mediated, ultrasoundpromoted chain extension of glycofuranosylamines with a propargyl group are reported. The procedure was applied to D-arabino and D-xylo substrates to give, via Cram-chelate transition states, 1-C-1-(3-trimethylsilyl-2-propynyl)-1-benzylamino pentionols in moderate to good yields and acceptable stereoselectivities (syn/anti >= 4: 1). To apply the reaction to the synthesis of galactofuranoside mimics, the D-xylo intermediate was cyclized to afford a 1-C-1-(2-propynyl)-1,4-dideoxy-1,4-imino-L-arabinitol derivative in excellent yield. This building block was used in three examples of CuAAC click reactions with azide compounds to provide the corresponding galactofuranoside mimics.