(4R,5S)-5-Allyl-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester | 169055-07-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R,5S)-5-Allyl-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4R,5S)-4-(hydroxymethyl)-2,2-dimethyl-5-prop-2-enyl-1,3-oxazolidine-3-carboxylate
• CAS: 169055-07-6
• 化学式: C₁₄H₂₅NO₄
• 分子量: 271.357
• InChiKey: NCKVYFLUYQBHKZ-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5S)-5-Allyl-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 sodium hydroxide 、 偶氮二甲酸二异丙酯 、 一水合肼 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 38.0h， 生成 (4R,5S)-5-Allyl-4-(benzyloxycarbonylamino-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Pseudodistomin C, a new piperidine alkaloid with unusual absolute configuration from the Okinawan tunicate Pseudodistoma kanoko

  摘要：

  Pseudodistomin C, a new cytotoxic piperidine alkaloid, was isolated from the Okinawan tunicate Pseudodistoma kanoko and the structure elucidated by spectral data, chemical degradations, and synthesis. The absolute configurations of the C-4 and C-5 chiral centers of pseudodistomin C were revealed by chiral HPLC analysis to be 4S and 5R, which were opposite to those of pseudodistomins A and B, previously isolated from the same tunicate, having the same planar structure as to the piperidine nucleus.

  DOI：

  10.1021/jo00126a053
• 作为产物：
  描述：

  2,2-Dimethyl-propionic acid (2S,3R)-2-tert-butoxycarbonylamino-3-hydroxy-hex-5-enyl ester 在 氢氧化钾 、 三氟化硼乙醚 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.33h， 生成 (4R,5S)-5-Allyl-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Pseudodistomin C, a new piperidine alkaloid with unusual absolute configuration from the Okinawan tunicate Pseudodistoma kanoko

  摘要：

  Pseudodistomin C, a new cytotoxic piperidine alkaloid, was isolated from the Okinawan tunicate Pseudodistoma kanoko and the structure elucidated by spectral data, chemical degradations, and synthesis. The absolute configurations of the C-4 and C-5 chiral centers of pseudodistomin C were revealed by chiral HPLC analysis to be 4S and 5R, which were opposite to those of pseudodistomins A and B, previously isolated from the same tunicate, having the same planar structure as to the piperidine nucleus.

  DOI：

  10.1021/jo00126a053

文献信息

• Total synthesis of pseudodistomin C, a sphingosine-related piperidine alkaloid from tunicate Pseudodistoma kanoko
  作者：Yukiko Doi、Masami Ishibashi、Jun'ichi Kobayashi

  DOI：10.1016/0040-4020(96)00137-8

  日期：1996.3

  Pseudodistomin C (1), a piperidine alkaloid isolated from the Okinawan tunicate Pseudodistoma kanoko, has been synthesized from d-serine to provide a further unambiguous evidence for the whole structure of 1 which possessed the opposite absolute configurations at the C-4 and C-5 chiral centers from those of pseudodistomins A (2) and B (3) obtained from the same tunicate.

  从d-丝氨酸合成了从冲绳被膜Pseudodistoma kanoko分离出的哌啶生物碱Pseudodistomin C（1），它为d的整个结构提供了进一步的明确证据，1在C-4和C-上具有相反的绝对构型。从假瘤菌素A（2）和B（3）的5个手性中心得自同一被膜。