(2S,3R,4R,5R)-1,3,4-tris(phenylmethyloxy)-5-{[(1,1-dimethylethoxy)carbonyl]amino}hexadec-15-en-2-ol | 651321-44-7

• 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,3R,4R,5R)-1,3,4-tris(phenylmethyloxy)-5-{[(1,1-dimethylethoxy)carbonyl]amino}hexadec-15-en-2-ol
• 英文别名: tert-butyl N-[(2S,3R,4R,5R)-2-hydroxy-1,3,4-tris(phenylmethoxy)hexadec-15-en-5-yl]carbamate
• CAS: 651321-44-7
• 化学式: C₄₂H₅₉NO₆
• 分子量: 673.934
• InChiKey: APPFTISWKAVQGL-KKOUMEGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  49
• 可旋转键数：
  26
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5R)-1,3,4-tris(phenylmethyloxy)-5-{[(1,1-dimethylethoxy)carbonyl]amino}hexadec-15-en-2-ol 在 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.58h， 生成 (2R,3R,4R,5R)-N-[(1,1-dimethylethoxy)carbonyl]-2-[(phenylmethoxy)methyl]-3,4-bis(phenylmethyloxy)-5-(undec-1-en-11-yl)pyrrolidine
  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：

  magnesium,undec-1-ene,bromide 在 盐酸 、 sodium hydroxide 、 三氯化铝 、 sodium azide 、 硼烷-三甲胺络合物 、 水 、 对甲苯磺酸 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.61h， 生成 (2S,3R,4R,5R)-1,3,4-tris(phenylmethyloxy)-5-{[(1,1-dimethylethoxy)carbonyl]amino}hexadec-15-en-2-ol
  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