(2R,3R,4R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-1-ol | 290834-34-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R,3R,4R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-1-ol
• 英文别名: [(2R,3R,4R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-1-hydroxypyrrolidin-2-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 290834-34-3
• 化学式: C₂₃H₅₃NO₄Si₃
• 分子量: 491.935
• InChiKey: HOYREHNRLWQMQP-VAMGGRTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.86
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-1-ol 在 氢氟酸 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 以100%的产率得到(2R,3R,4R)-2-Hydroxymethyl-pyrrolidine-1,3,4-triol
  参考文献：
  名称：

  Synthesis of a novel N-hydroxypyrrolidine using enzyme catalysed asymmetric carbon–carbon bond synthesis

  摘要：

  N-Hydroxypyrrolidine 5 has been prepared in nine steps starting from;3-O-benzylglyceraldehyde 13. The synthetic route employs Escherichia coli transketolase mediated C-C bond synthesis to establish the absolute stereochemistry and a subsequent ring contraction of a 1,2-oxazine 17 to provide the N-hydroxypyrrolidine nucleus. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00645-6
• 作为产物：
  描述：

  (4R,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-6-ethoxy-5,6-dihydro-4H-[1,2]oxazine 在 sodium cyanoborohydride 作用下， 以 溶剂黄146 为溶剂， 以37%的产率得到(2R,3R,4R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-1-ol
  参考文献：
  名称：

  Synthesis of a novel N-hydroxypyrrolidine using enzyme catalysed asymmetric carbon–carbon bond synthesis

  摘要：

  N-Hydroxypyrrolidine 5 has been prepared in nine steps starting from;3-O-benzylglyceraldehyde 13. The synthetic route employs Escherichia coli transketolase mediated C-C bond synthesis to establish the absolute stereochemistry and a subsequent ring contraction of a 1,2-oxazine 17 to provide the N-hydroxypyrrolidine nucleus. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00645-6