2-hydroxy-3-(4-methyl benzenesulfonylamino)-3-phenyl-propionic acid methyl ester | 176298-46-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-hydroxy-3-(4-methyl benzenesulfonylamino)-3-phenyl-propionic acid methyl ester
• 英文别名: methyl (2R,3S)-N-(p-toluenesulfonyl)-3-amino-3-phenyl-2-hydroxypropanoate；(2R,3S)-methyl 2-hydroxy-3-(p-toluenesulfonamido)-3-phenylpropionate；(2R,3S)-(+)-methyl-N-(p-toluenesulfonyl)-2-hydroxy-3-amino-3-phenyl propionate；methyl (2R,3S)-2-hydroxy-3-[(4-methylphenyl)sulfonylamino]-3-phenylpropanoate
• CAS: 176298-46-7
• 化学式: C₁₇H₁₉NO₅S
• 分子量: 349.408
• InChiKey: KLQHTVJOCDVCHB-JKSUJKDBSA-N

物化性质

• 熔点：
  140-145 °C(Solv: acetonitrile (75-05-8); water (7732-18-5))
• 沸点：
  534.4±60.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3-(4-methyl benzenesulfonylamino)-3-phenyl-propionic acid methyl ester 在 ruthenium trichloride 盐酸 、 过碘酸 作用下， 生成 (2S)-2-phenyl-2-(tosylamino)acetic acid
  参考文献：
  名称：

  Novel Asymmetric C−C Bond Formation Process Promoted by Et₂AlCl and Its Application to the Stereoselective Synthesis of Unusual β-Branched Baylis−Hillman Adducts

  摘要：

  DOI：

  10.1021/jo981976l
• 作为产物：
  描述：

  N-苯甲酰基-(2R,3S)-3-苯基异丝氨酸甲酯 在 盐酸 、 氯化亚砜 、 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 生成 2-hydroxy-3-(4-methyl benzenesulfonylamino)-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  Li, Guigen; Chang, Han-Ting; Sharpless, K. Barry, Angewandte Chemie, 1996, vol. 108, # 4, p. 449 - 452

  摘要：

  DOI：

文献信息

• Synthesis and Anti-HBV Activity of Novel 3′-N-phenylsulfonyl Docetaxel Analogs
  作者：Jun Chang、Yun-Peng Hao、Xiao-Dong Hao、Hong-Fu Lu、Jian-Ming Yu、Xun Sun

  DOI：10.3390/molecules180910189

  日期：——

  Nine new 3′-N-phenylsulfonyl docetaxel analogs were synthesized in good yields from the key intermediate N-phenylsulfonyl oxazolidine via a six-step route. These analogs were tested for anti-hepatitis B virus (HBV) activity in vitro. Compounds 3e, 3g and 3j showed more potent inhibitory activity against HBeAg secretion than the positive control lamivudine. Further extensive SAR and mechanistic studies will be reported in due course.

  合成了九种新的3′-N-苯磺酰多西他赛类似物，产率良好，采用六步法从关键中间体N-苯磺酰噁唑烷合成。这些类似物在体外测试了抗乙型肝炎病毒（HBV）活性。化合物3e、3g和3j对HBeAg分泌的抑制活性比阳性对照拉米夫定更强。进一步的广泛SAR和机制研究将适时报告。
• A Highly Efficient Aminohydroxylation Process
  作者：A. Erik Rubin、K. Barry Sharpless

  DOI：10.1002/anie.199726371

  日期：1997.12.15
• Osmium-catalyzed vicinal oxyamination of olefins by Chloramine-T
  作者：K. B. Sharpless、A. O. Chong、Koichiro Oshima

  DOI：10.1021/jo00863a052

  日期：1976.1
• Design, synthesis of novel C-3′-N-sulfonyl modified taxane analogues from 1-deoxybaccatin VI and their impact on anti-HCC activity
  作者：Yan-Ru Xiao、Yong-Mei Cui、Cheng-Hu Xie、Wei-Qing Qiu、Hai-Xia Lin

  DOI：10.1080/10286020.2019.1691999

  日期：2020.12.1

  A new series of C-3 '-N-sulfonyl paclitaxel analogs were designed and synthesized from 1-deoxybaccatin VI and their structures were confirmed by H-1 NMR, C-13 NMR and high resolution MS. The synthesized compounds were evaluated for their in vitro anti-Hepatocellular carcinoma (HCC) activity against human hepatoma (HepG2) cell line. Bioassay results showed that compounds 17c, 17d and 17f exhibited more potent inhibitory activity against HepG2 cell line in comparison with paclitaxel. It is suggested that paclitaxel analogs containing the C-3 '-N-sulfonyl could be considered as a precursor structure for further synthesis of more potent analogues.
• Concise and diastereoselective approach to syn- and anti-N-tosyl-α-hydroxy β-amino acid derivatives
  作者：Yonghua Zhao、Nan Jiang、Shufeng Chen、Cheng Peng、Xiaomei Zhang、Yaping Zou、Shiwei Zhang、Jianbo Wang

  DOI：10.1016/j.tet.2005.04.054

  日期：2005.7

  The methyl diazoacetate and aryl (N-tosyl)imines can be transformed into syn or anti a-hydroxy P-amino esters with high diastereoselectivities in three steps: the base promoted nucleophilic condensation of the methyl diazoacetate and aryl (N-tosyl)imines to give beta-(N-tosyl)amino alpha-diazoesters, followed by oxidation with Oxoneo to generate alpha-oxo esters, which were reduced with NaBH4 to yield the anti-N-losyl-alpha-hydroxy beta-amino ester, or hydrogenated with Pd/C (10%) as the catalyst to yield corresponding syn isomer, both in high diastereoselectivity. (c) 2005 Elsevier Ltd. All rights reserved.