N-Boc-broussonetine C | 651321-51-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-Boc-broussonetine C
• CAS: 651321-51-6
• 化学式: C₂₃H₄₃NO₇
• 分子量: 445.597
• InChiKey: LBFYWLCGGPVJRT-XRXFAXGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  31.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  127.53
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-Boc-broussonetine C 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以60%的产率得到13-[(2R,3R,4R,5R)-3,4-二羟基-5-(羟甲基)吡咯烷-2-基]-1-羟基十三烷-4-酮
  参考文献：
  名称：

  An Asymmetric Total Synthesis of Broussonetine C

  摘要：

  Broussonetine C, a member of the Broussonetia class, was first isolated from the branches of Broussonetia Kazinoki (a deciduous tree distributed throughout Japan, China and Taiwan) in 1997 by Kusano et al.([1,2]) and was assigned structure 1. All of the Broussonetines incorporate a 2,3,4,5-tetrasubstituted pyrrolidine unit as a key motif, probably the most synthetically challenging substructure associated with this class of natural product. Significantly, Broussonetine C was found to exhibit unique beta-galactosidase and beta-mannosidase activities.([1,2]) Such properties, coupled with the unique structure assigned to the alkaloid encouraged us to choose 1 as a novel synthetic target. Thus far, only one asymmetric total synthesis of this pyrrolidine alkaloid has been reported. ([3]) In this report we describe a synthesis of 1, starting from D-arabinose.

  DOI：

  10.1081/car-120026470
• 作为产物：
  描述：

  (2R,3R,4R,5R)-N-[(1,1-dimethylethoxy)carbonyl]-2-[(phenylmethoxy)methyl]-3,4-bis(phenylmethyloxy)-5-(1,2-dihydroxyundecan-11-yl)pyrrolidine 在 palladium on activated charcoal sodium periodate 、 氢气 、 戴斯-马丁氧化剂 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 26.0h， 生成 N-Boc-broussonetine C
  参考文献：
  名称：

  An Asymmetric Total Synthesis of Broussonetine C

  摘要：

  Broussonetine C, a member of the Broussonetia class, was first isolated from the branches of Broussonetia Kazinoki (a deciduous tree distributed throughout Japan, China and Taiwan) in 1997 by Kusano et al.([1,2]) and was assigned structure 1. All of the Broussonetines incorporate a 2,3,4,5-tetrasubstituted pyrrolidine unit as a key motif, probably the most synthetically challenging substructure associated with this class of natural product. Significantly, Broussonetine C was found to exhibit unique beta-galactosidase and beta-mannosidase activities.([1,2]) Such properties, coupled with the unique structure assigned to the alkaloid encouraged us to choose 1 as a novel synthetic target. Thus far, only one asymmetric total synthesis of this pyrrolidine alkaloid has been reported. ([3]) In this report we describe a synthesis of 1, starting from D-arabinose.

  DOI：

  10.1081/car-120026470