(4R,5R)-4-hydroxymethyl-5-methoxycarbonylmethyloxazolidine-3-carboxylic acid tert-butyl ester | 1213789-90-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-4-hydroxymethyl-5-methoxycarbonylmethyloxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4R,5R)-4-(hydroxymethyl)-5-(2-methoxy-2-oxoethyl)-1,3-oxazolidine-3-carboxylate
• CAS: 1213789-90-2
• 化学式: C₁₂H₂₁NO₆
• 分子量: 275.302
• InChiKey: ZRENZYWDRMRGAO-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R,5R)-4-hydroxymethyl-5-methoxycarbonylmethyloxazolidine-3-carboxylic acid tert-butyl ester 在 sodium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物 、 碳酸氢钠 、 potassium bromide 、 盐酸 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 以97%的产率得到(4S,5R)-5-methoxycarbonylmethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester
  参考文献：
  名称：

  Efficient and stereoselective synthesis of threo-β-hydroxy-l-glutamic acid via a tandem (Z)-olefination-conjugate addition

  摘要：

  threo-beta-Hydroxy-L-glutamic acid I is an attractive target as a biologically active compound and as a chiral synthon. The required beta-hydroxyl group in 1 was efficiently and stereoselectively introduced via an intramolecular conjugate addition of the N-hydroxymethyl group of gamma-amino-alpha,beta-unsaturated (Z)-ester 4. While the corresponding (E)-ester 3 gave a lower selectivity of ca. 5:1 in the intramolecular conjugate addition, a selectivity of up to 70:1 was shown with (Z)-ester 4. The tandem (Z)-olefination-conjugate addition could be achieved by simply changing the reaction conditions to give a selectivity of >20:1. Thus, the target compound I was obtained as its hydrochloride salt in 70% overall yield over four steps from lactol 2. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.023
• 作为产物：
  描述：

  (4S,5R)-4-(tert-butyldimethylsilyloxymethyl)-5-methoxycarbonylmethyloxazolidine-3-carboxylic acid tert-butyl ester 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以82%的产率得到(4R,5R)-4-hydroxymethyl-5-methoxycarbonylmethyloxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Efficient and stereoselective synthesis of threo-β-hydroxy-l-glutamic acid via a tandem (Z)-olefination-conjugate addition

  摘要：

  threo-beta-Hydroxy-L-glutamic acid I is an attractive target as a biologically active compound and as a chiral synthon. The required beta-hydroxyl group in 1 was efficiently and stereoselectively introduced via an intramolecular conjugate addition of the N-hydroxymethyl group of gamma-amino-alpha,beta-unsaturated (Z)-ester 4. While the corresponding (E)-ester 3 gave a lower selectivity of ca. 5:1 in the intramolecular conjugate addition, a selectivity of up to 70:1 was shown with (Z)-ester 4. The tandem (Z)-olefination-conjugate addition could be achieved by simply changing the reaction conditions to give a selectivity of >20:1. Thus, the target compound I was obtained as its hydrochloride salt in 70% overall yield over four steps from lactol 2. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.023

文献信息

• Efficient and stereoselective synthesis of threo-β-hydroxy-l-glutamic acid via a tandem (Z)-olefination-conjugate addition
  作者：Hyeonjeong Kim、Dongwon Yoo、Seah Kwon、Young Gyu Kim

  DOI：10.1016/j.tetasy.2009.11.023

  日期：2009.12

  threo-beta-Hydroxy-L-glutamic acid I is an attractive target as a biologically active compound and as a chiral synthon. The required beta-hydroxyl group in 1 was efficiently and stereoselectively introduced via an intramolecular conjugate addition of the N-hydroxymethyl group of gamma-amino-alpha,beta-unsaturated (Z)-ester 4. While the corresponding (E)-ester 3 gave a lower selectivity of ca. 5:1 in the intramolecular conjugate addition, a selectivity of up to 70:1 was shown with (Z)-ester 4. The tandem (Z)-olefination-conjugate addition could be achieved by simply changing the reaction conditions to give a selectivity of >20:1. Thus, the target compound I was obtained as its hydrochloride salt in 70% overall yield over four steps from lactol 2. (C) 2009 Elsevier Ltd. All rights reserved.