2,3-di-O-benzyl-5-O-tert-butyl(dimethyl)silyl-D-arabinose | 651321-34-5

• 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-di-O-benzyl-5-O-tert-butyl(dimethyl)silyl-D-arabinose
• 英文别名: (2S,3R,4R)-5-[tert-butyl(dimethyl)silyl]oxy-4-hydroxy-2,3-bis(phenylmethoxy)pentanal
• CAS: 651321-34-5
• 化学式: C₂₅H₃₆O₅Si
• 分子量: 444.643
• InChiKey: FNOJLUHRMLGZHZ-WXFUMESZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-di-O-benzyl-5-O-tert-butyl(dimethyl)silyl-D-arabinose 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 potassium osmate(VI) 、 sodium periodate 、 三氯化铝 、 sodium azide 、 N-甲基吲哚酮 、 硼烷-三甲胺络合物 、 potassium tert-butylate 、 水 、 氢气 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 106.19h， 生成 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,4S)-3,4-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-5,5-bis-ethylsulfanyl-pentan-2-ol 在 mercury dichloride 、 mercury(II) oxide 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 生成 2,3-di-O-benzyl-5-O-tert-butyl(dimethyl)silyl-D-arabinose
  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

文献信息

• An Asymmetric Total Synthesis of Broussonetine C
  作者：Patrick Perlmutter、Filisaty Vounatsos

  DOI：10.1081/car-120026470

  日期：2003.12.31

  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.