(αRS,βRS)-N-[(benzyloxy)carbonyl]-β-hydroxy-phenylalanine | 5817-49-2

• 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: (αRS,βRS)-N-[(benzyloxy)carbonyl]-β-hydroxy-phenylalanine
• 英文别名: N-benzyloxycarbonyl-DL-threo-β-phenylserine；DL-threo-α-Benzyloxycarbonylamino-β-phenyl-serin；(2R,3R)-3-hydroxy-3-phenyl-2-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 5817-49-2；5817-50-5；32899-57-3；32926-35-5；93921-03-0；99147-22-5
• 化学式: C₁₇H₁₇NO₅
• 分子量: 315.326
• InChiKey: SYNFYDJGTLTEFE-HUUCEWRRSA-N

物化性质

• 熔点：
  78-80 °C
• 沸点：
  557.7±50.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (αRS,βRS)-N-[(benzyloxy)carbonyl]-β-hydroxy-phenylalanine 在 lithium aluminium tetrahydride 、 五氯化磷 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.33h， 生成 (Z)-4-benzylideneoxazolidine-2-one
  参考文献：
  名称：

  Jones, John H.; Witty, Michael J., Journal of the Chemical Society. Perkin transactions I, 1980, p. 858 - 864

  摘要：

  DOI：
• 作为产物：
  描述：

  (3RS)-7-氯-1,3-二氢-3-[(1SR)-羟基(苯基)甲基]-1-甲基-5-苯基-2H-1,4-苯并二氮杂-2-酮 在 盐酸 、 水 作用下， 以 甲醇 、 水 为溶剂， 反应 34.0h， 生成 (αRS,βRS)-N-[(benzyloxy)carbonyl]-β-hydroxy-phenylalanine
  参考文献：
  名称：

  摘要：

  The aldol reaction of the C(3) carbanion of 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one (2) with a series of aromatic and aliphatic aldehydes at -78 degrees afforded threolerythro diastereoisomers 3-16 of 7-chloro-1,3-dihydro-3-(hydroxymethyl)-1-methyl-5-phenyl-2H-1,4-benzodiazepinones, substituted at the C(3) side chain, in a ratio from 55:45 to 94:6 (Scheme 1). Lewis acids exhibited limited effect on the syn/ anti diastereoselectivity of this reaction, and kinetic control of the reaction was confirmed. H-1-NMR Data suggested the assignment of the threo relative configuration to the first-eluted diastereoisomers 3, 5, 7,and 9 on reversed-phase HPLC, and the erythro configuration to the second-eluted counterparts 4, 6, 8, and 10, respectively. The structures and relative configurations three and erythro of the diastereoisomers 5 and 6, respectively, were established by single-crystal X-ray analysis, confirming the assignment based on the H-1-NMR data. A tentative mechanistic explanation of the diastereoselectivity invokes the enolate anion of 1,3-dihydro-2H-1,4-benzodiazepin-2-one as the reactive species (Scheme 2). Acid-catalyzed hydrolytic ring opening of 3 afforded threo-beta-hydroxy-phenylalanine 17, whereas from 4, the N-(benzyloxy)carbonyl derivative 18 of erythro-beta-hydroxy-phenylalanine was obtained (Scheme 3); in both cases, neither elimination of H2O from the C(3)-CHOH moiety nor epimerization at C(3) were observed. This result opens a new pathway to various configurationally uniform alpha-amino-beta-hydroxy carboxylic acids and their congeners of biological importance.

  DOI：

  10.1002/(sici)1522-2675(20000315)83:3<603::aid-hlca603>3.0.co;2-1

文献信息

• GB836332
  申请人：——

  公开号：——

  公开（公告）日：——
• 272. Derivatives of 6-aminopenicillanic acid. Part I. α-Aminobenzylpenicillin and some related compounds
  作者：F. P. Doyle、G. R. Fosker、J. H. C. Nayler、H. Smith

  DOI：10.1039/jr9620001440

  日期：——
• ——
  作者：Dean Marković、Zdenko Hameršak、Aleksandar Višnjevac、Biserka Kojić-Prodić、Vitomir Šunjić

  DOI：10.1002/(sici)1522-2675(20000315)83:3<603::aid-hlca603>3.0.co;2-1

  日期：2000.3.15

  The aldol reaction of the C(3) carbanion of 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one (2) with a series of aromatic and aliphatic aldehydes at -78 degrees afforded threolerythro diastereoisomers 3-16 of 7-chloro-1,3-dihydro-3-(hydroxymethyl)-1-methyl-5-phenyl-2H-1,4-benzodiazepinones, substituted at the C(3) side chain, in a ratio from 55:45 to 94:6 (Scheme 1). Lewis acids exhibited limited effect on the syn/ anti diastereoselectivity of this reaction, and kinetic control of the reaction was confirmed. H-1-NMR Data suggested the assignment of the threo relative configuration to the first-eluted diastereoisomers 3, 5, 7,and 9 on reversed-phase HPLC, and the erythro configuration to the second-eluted counterparts 4, 6, 8, and 10, respectively. The structures and relative configurations three and erythro of the diastereoisomers 5 and 6, respectively, were established by single-crystal X-ray analysis, confirming the assignment based on the H-1-NMR data. A tentative mechanistic explanation of the diastereoselectivity invokes the enolate anion of 1,3-dihydro-2H-1,4-benzodiazepin-2-one as the reactive species (Scheme 2). Acid-catalyzed hydrolytic ring opening of 3 afforded threo-beta-hydroxy-phenylalanine 17, whereas from 4, the N-(benzyloxy)carbonyl derivative 18 of erythro-beta-hydroxy-phenylalanine was obtained (Scheme 3); in both cases, neither elimination of H2O from the C(3)-CHOH moiety nor epimerization at C(3) were observed. This result opens a new pathway to various configurationally uniform alpha-amino-beta-hydroxy carboxylic acids and their congeners of biological importance.
• Jones, John H.; Witty, Michael J., Journal of the Chemical Society. Perkin transactions I, 1980, p. 858 - 864
  作者：Jones, John H.、Witty, Michael J.

  DOI：——

  日期：——