tert-butyl (3aR,4S,6aS)-4-[(2R,3R)-2,3-dihydroxy-4-(4-methylphenyl)sulfonyloxybutyl]-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate | 479665-67-3

• 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: tert-butyl (3aR,4S,6aS)-4-[(2R,3R)-2,3-dihydroxy-4-(4-methylphenyl)sulfonyloxybutyl]-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• CAS: 479665-67-3
• 化学式: C₂₃H₃₅NO₉S
• 分子量: 501.598
• InChiKey: MRNNPVCDBUPIMY-MFKWGIFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl (3aR,4S,6aS)-4-[(2R,3R)-2,3-dihydroxy-4-(4-methylphenyl)sulfonyloxybutyl]-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate 在 ammonium hydroxide 、 三氟乙酸 作用下， 反应 2.0h， 生成 (1R,2S,6R,7R,8aS)-1,2,6,7-tetrahydroxyindolizidine
  参考文献：
  名称：

  A convenient stereoselective route to novel tetrahydroxyindolizidines

  摘要：

  A convenient stereoselective route, for the preparation of novel tetrahydroxyindolizidines, based on syn-hydroxylation reactions of alkenyl pyrrolidines followed by cyclization, is reported. Derivatives of (+)-swainsonine are prepared. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02084-1
• 作为产物：
  描述：

  3,6-(tert-butoxycarbonyl)imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexose 在 吡啶 、 4-二甲氨基吡啶 、 甲基磺酰胺 、 Py-PIP 、 TEA 、 sodium methylate 、 二异丁基氢化铝 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 56.0h， 生成 tert-butyl (3aR,4S,6aS)-4-[(2R,3R)-2,3-dihydroxy-4-(4-methylphenyl)sulfonyloxybutyl]-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
  参考文献：
  名称：

  A convenient stereoselective route to novel tetrahydroxyindolizidines

  摘要：

  A convenient stereoselective route, for the preparation of novel tetrahydroxyindolizidines, based on syn-hydroxylation reactions of alkenyl pyrrolidines followed by cyclization, is reported. Derivatives of (+)-swainsonine are prepared. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02084-1

文献信息

• A convenient stereoselective route to novel tetrahydroxyindolizidines
  作者：Ana T. Carmona、José Fuentes、Inmaculada Robina

  DOI：10.1016/s0040-4039(02)02084-1

  日期：2002.11

  A convenient stereoselective route, for the preparation of novel tetrahydroxyindolizidines, based on syn-hydroxylation reactions of alkenyl pyrrolidines followed by cyclization, is reported. Derivatives of (+)-swainsonine are prepared. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Carmona, Ana T.; Fuentes, Jose; Robina, Inmaculada, Journal of Organic Chemistry, 2003, vol. 68, # 10, p. 3874 - 3883
  作者：Carmona, Ana T.、Fuentes, Jose、Robina, Inmaculada、Garcia, Eliazar Rodriguez、Demange, Raynald、Vogel, Pierre、Winters, Ana L.

  DOI：——

  日期：——