187039-57-2 N-Boc-(2S,3S)-3-羟基-2-羧基吡咯烷

中文名称: N-Boc-(2S,3S)-3-羟基-2-羧基吡咯烷
英文名称: (2S,3S)-1-(tert-Butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid
CAS号
分子式: C₁₀H₁₇NO₅
分子量: 231.25
更新日期: 2026-06-23

名称和标识

中文名: N-Boc-(2S,3S)-3-羟基-2-羧基吡咯烷
英文名: (2S,3S)-1-(tert-Butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid
CAS号: 187039-57-2
分子式: C10H17NO5
分子量: 231.25
中文别名: Boc-反式-3-羟基-l-脯氨酸; (2S,3S)-3-羟基-1,2-吡咯烷二甲酸 1-叔丁酯; BOC-反-3-羟基-L-脯氨酸; (2S,3S)-3-羟基-吡咯烷-1,2-二羧酸1-叔丁酯; (2S,3S)-1-[(叔-丁氧基)羰基]-3-羟基吡咯烷-2-羧酸; 反式-N-BOC-3-羟基-L-脯氨酸; (2S,3S)-N-BOC-3-羟基-L-脯氨酸
英文别名: (2S,3S)-3-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid; N-tert-butoxycarbonyl-trans-3-hydroxy-L-proline; (2S,3S)-3-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester; Boc-(2S,3S)-3-Hydroxypyrrolidine-2-carboxylic acid; (2S,3S)-1-(tert-butoxycarbonyl)-3-hydroxyproline; (3S)-3-Hydroxy-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-proline; (3S)-1-(tert-butoxycarbonyl)-3-hydroxy-L-proline; Boc-trans-3-hydroxy-L-proline; (2S,3S)-1-[(tert-butoxy)carbonyl]-3-hydroxypyrrolidine-2-carboxylic acid; Boc-trans-3-OH-Pro-OH; (2S,3S)-1-BOC-3-hydroxypyrrolidine-2-carboxylic acid; (2S,3S)-N-Boc-3-hydroxy-L-proline; N-(tert-butoxycarbonyl)-trans-3-hydroxy-L-proline; BOC-(2S,3S)-3-Hydroxy-2-pyrrolidinecarboxylic acid; (2S,3S)-N-Boc-3-hydroxypyrrolidine-2-carboxylic acid; N-Boc-(2S,3S)-3-hydroxypyrrolidine-2-carboxylic acid; (2S,3S)-1-(tert-butoxycarbonyl)-2-carboxy-3-hydroxypyrrolidine; trans-3-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

物化属性

LogP: -0.54
LogS: -1.52
PSA: 87.07 Å²
XLogP3-AA: 0.8
pKa: 3.69±0.40 (Predicted)
储存条件: 室温
分子量: 231.25 g/mol
单同位素质量: 231.11067264
可旋转键数量: 3
合成可及性: 3.09
外观: 白色至浅棕色固体
密度: 1.3±0.1 g/cm³
折射率: 1.531
摩尔折射率: 59.53
氢键供体数量: 2
氢键受体数量: 5
沸点: 390.9±42.0 °C (760 mmHg)
溶解度: 6.98 mg/ml ; 0.0302 mol/l
熔点: 157 °C
皮肤渗透系数: -7.14 cm/s
精确质量: 231.11067264
蒸汽压: 0.0±2.0 mmHg (25 °C)
闪点: 190.2±27.9 °C

安全信息

安全说明

运输方式：冰袋运输。危险描述：非危险化学品，危险等级为IRRITANT（刺激性）。

生产及用途

用途与制备

化学合成

路线1：

步骤: 向1-(叔丁氧基羰基)-2-甲基-(2S,3S)-3-羟基吡咯烷-1,2-二甲酸酯的四氢呋喃溶液中加入0.2N氢氧化锂水溶液，室温搅拌3小时；反应完成后用乙醚稀释，水层用5%盐酸酸化至pH=2，乙酸乙酯萃取，有机层干燥浓缩得产物。
条件: 20℃；四氢呋喃-水体系；0.2N LiOH水溶液；3小时
收率: 88%
参考文献: Patent: WO2016/7534, 2016, A1. Location in patent: Page/Page column 171; 172

路线2：

步骤: 实施例24A（2S，3S）-3-羟基-吡咯烷-1,2-二羧酸1-叔丁基酯3-羟基-吡咯烷-2-羧酸与二碳酸二叔丁酯、NaOH在室温下处理2小时；0-10℃用5%HCl酸化至pH=4，乙酸乙酯萃取，合并萃取物用盐水洗涤，真空浓缩得产物。
条件: 20℃（第一步）；0-10℃（第二步）；水体系；NaOH水溶液；HCl水溶液；2小时（第一步）
收率: 86%
参考文献: Patent: US2005/101602, 2005, A1. Location in patent: Page/Page column 35-36

路线3：

步骤: 向羧酸的四氢呋喃溶液中加入二碳酸二叔丁酯和碳酸氢钠水溶液，低温（0℃）升至室温搅拌16小时；浓缩后水稀释，乙醚萃取，水层用6N HCl酸化，二氯甲烷萃取，合并有机层浓缩并与甲苯共蒸发，高真空干燥得产物。
条件: 0-20℃；四氢呋喃-水体系；碳酸氢钠水溶液；16小时；二氯甲烷萃取
收率: 91%
参考文献: Journal of Medicinal Chemistry, 2006, vol. 49, #21, p. 6254 - 6263; Tetrahedron Letters, 2009, vol. 50, #52, p. 7280 - 7282; Tetrahedron Letters, 1997, vol. 38, #2, p. 167 - 168; Patent: US2010/22605, 2010, A1. Location in patent: Page/Page column 16; 33; 36; Patent: WO2008/24725, 2008, A1. Location in patent: Page/Page column 130-131; Patent: WO2009/140448, 2009, A1. Location in patent: Page/Page column 32; Patent: WO2004/7501, 2004, A1. Location in patent: Page 504-505; Journal of the American Chemical Society, 2005, vol. 127, #45, p. 15923 - 15932; Patent: US2002/19388, 2002, A1; Patent: EP1428824, 2004, A1. Location in patent: Page 50; Patent: US2005/209217, 2005, A1. Location in patent: Page/Page column 27; European Journal of Organic Chemistry, 2009, #20, p. 3368 - 3386; Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, #23, p. 5478 - 5483; Patent: EP2419404, 2015, B1. Location in patent: Paragraph 0504; Patent: WO2016/25669, 2016, A1. Location in patent: Page/Page column 72; Patent: WO2017/63757, 2017, A1. Location in patent: Page/Page column 45

词条详情加载中…