N-benzyl-2,3,5-tri-O-benzyl-L-arabinofuranosylamine | 172488-47-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-benzyl-2,3,5-tri-O-benzyl-L-arabinofuranosylamine
• 英文别名: (3R,4S,5S)-N-benzyl-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-amine
• CAS: 172488-47-0
• 化学式: C₃₃H₃₅NO₄
• 分子量: 509.645
• InChiKey: IMHITWXSYMTQBM-HBJVCUMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzyl-2,3,5-tri-O-benzyl-L-arabinofuranosylamine 在 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (3R,4S,5R)-1-Benzyl-3,4-bis-benzyloxy-5-(4-methoxy-benzyl)-pyrrolidin-2-one
  参考文献：
  名称：

  A Short Synthetic Approach to Enantiomerically Pure (-)-Anisomycin

  摘要：

  A convenient enantiomerically pure route to an antibiotic, natural (-)-anisomycin has been developed in a short number of steps by featuring the stereocontrolled elaboration of the functionalized homochiral lactam derived from 2,3,5-tri-O-benzyl-beta-L-arabinofuranose involving no separation of stereoisomers through the entire sequence.

  DOI：

  10.3987/com-95-7214
• 作为产物：
  描述：

  2,3,5-tri-O-benzyl-α-L-arabinofuranose 、 苄胺 在 MS 4A 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到N-benzyl-2,3,5-tri-O-benzyl-L-arabinofuranosylamine
  参考文献：
  名称：

  A Short Synthetic Approach to Enantiomerically Pure (-)-Anisomycin

  摘要：

  A convenient enantiomerically pure route to an antibiotic, natural (-)-anisomycin has been developed in a short number of steps by featuring the stereocontrolled elaboration of the functionalized homochiral lactam derived from 2,3,5-tri-O-benzyl-beta-L-arabinofuranose involving no separation of stereoisomers through the entire sequence.

  DOI：

  10.3987/com-95-7214

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.
• A Short Synthetic Approach to Enantiomerically Pure (-)-Anisomycin
  作者：Hidemi Yoda、Tomohito Nakajima、Hiroyasu Yamazaki、Kunihiko Takabe

  DOI：10.3987/com-95-7214

  日期：——

  A convenient enantiomerically pure route to an antibiotic, natural (-)-anisomycin has been developed in a short number of steps by featuring the stereocontrolled elaboration of the functionalized homochiral lactam derived from 2,3,5-tri-O-benzyl-beta-L-arabinofuranose involving no separation of stereoisomers through the entire sequence.