6-{(3S,5R)-2-Benzyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(2-methoxy-ethoxymethoxy)-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl ester | 220046-46-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-{(3S,5R)-2-Benzyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(2-methoxy-ethoxymethoxy)-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl ester
• 英文别名: methyl 6-[(3S,5R)-2-benzyl-5-[(1S,2R)-2-[tert-butyl(dimethyl)silyl]oxy-1-(2-methoxyethoxymethoxy)propyl]-1,2-oxazolidin-3-yl]hexanoate
• CAS: 220046-46-8
• 化学式: C₃₀H₅₃NO₇Si
• 分子量: 567.839
• InChiKey: JCWKDZAUYDKNHY-SQCBCDKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  39
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  75.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-{(3S,5R)-2-Benzyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(2-methoxy-ethoxymethoxy)-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 以70%的产率得到6-{(3S,5R)-2-Benzyl-5-[(1R,2R)-2-hydroxy-1-(2-methoxy-ethoxymethoxy)-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl ester
  参考文献：
  名称：

  Total synthesis of (+)-azimic acid, (+)-julifloridine, and proposed structure ofN-methyljulifloridine via cycloaddition of nitrone to a chiral dipolarophile

  摘要：

  A combination of 1,3-dipolar cycloaddition of Z-nitrones to the chiral dipolarophile and subsequent ring transformation of the resulting adducts to the piperidinols has provided a new practical synthesis of 2,6-disubstituted 3-piperidinol alkaloids, (+)-azimic acid, (+)-julifloridine, and the proposed structure of N-methyljulifloridine. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01012-6
• 作为产物：
  描述：

  2-甲氧基乙氧基甲基氯 、 6-{(3S,5R)-2-Benzyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl ester 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 以81%的产率得到6-{(3S,5R)-2-Benzyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(2-methoxy-ethoxymethoxy)-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl ester
  参考文献：
  名称：

  Total synthesis of (+)-azimic acid, (+)-julifloridine, and proposed structure ofN-methyljulifloridine via cycloaddition of nitrone to a chiral dipolarophile

  摘要：

  A combination of 1,3-dipolar cycloaddition of Z-nitrones to the chiral dipolarophile and subsequent ring transformation of the resulting adducts to the piperidinols has provided a new practical synthesis of 2,6-disubstituted 3-piperidinol alkaloids, (+)-azimic acid, (+)-julifloridine, and the proposed structure of N-methyljulifloridine. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01012-6

文献信息

• Total synthesis of (+)-azimic acid, (+)-julifloridine, and proposed structure ofN-methyljulifloridine via cycloaddition of nitrone to a chiral dipolarophile
  作者：Toshiko Kiguchi、Mitsuko Shirakawa、Rina Honda、Ichiya Ninomiya、Takeaki Naito

  DOI：10.1016/s0040-4020(98)01012-6

  日期：1998.12

  A combination of 1,3-dipolar cycloaddition of Z-nitrones to the chiral dipolarophile and subsequent ring transformation of the resulting adducts to the piperidinols has provided a new practical synthesis of 2,6-disubstituted 3-piperidinol alkaloids, (+)-azimic acid, (+)-julifloridine, and the proposed structure of N-methyljulifloridine. (C) 1998 Elsevier Science Ltd. All rights reserved.