(2S)-2-[(4-甲氧基苯基)甲氧基羰基氨基]-3-苯基丙酸 | 23234-86-8

• 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
• 中文名称: (2S)-2-[(4-甲氧基苯基)甲氧基羰基氨基]-3-苯基丙酸
• 英文名称: N-(4-methoxybenzyloxycarbonyl)-L-phenylalanine
• 英文别名: Z(OMe)-Phe-OH；pMZ-Phe-OH；N-(4-methoxybenzyloxycarbonyl)-L-phenyalanine；(2S)-2-[(4-methoxyphenyl)methoxycarbonylamino]-3-phenylpropanoic acid
• CAS: 23234-86-8
• 化学式: C₁₈H₁₉NO₅
• 分子量: 329.353
• InChiKey: UVWJYTBVDBCVGT-INIZCTEOSA-N

物化性质

• 熔点：
  83-84 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  543.2±50.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(4-甲氧基苯基)甲氧基羰基氨基]-3-苯基丙酸 在 三乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 H-Gly-Phe-Leu-OBzl
  参考文献：
  名称：

  Tsuji, Toshiki; Okusada, Satoshi; Maeda, Mitsuko, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 5, p. 2214 - 2217

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基苄醇 在 吡啶 、 magnesium oxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 (2S)-2-[(4-甲氧基苯基)甲氧基羰基氨基]-3-苯基丙酸
  参考文献：
  名称：

  Weygand,F.; Hunger,K., Chemische Berichte, 1962, vol. 95, p. 1 - 6

  摘要：

  DOI：

文献信息

• Carbonic acid esters, and the preparation thereof and their use
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04010178A1

  公开（公告）日：1977-03-01

  Carbonic acid esters of the formula substituent(s) substituents(s) R'.sub.1 OCOOR'.sub.2 wherein R'.sub.1 is lower alkyl which may have substituent)s) selected from the group of halogen, lower alkoxy and aryloxy, or ar(lower)-alkyl which may have substituents)s) selected from the group of lower alkoxy, halogen, nitro and cyano, and R'.sub.2 is benzotriazolyl which may have halogen; or a group represented by the formula: ##STR1## wherein Y' and Z' are each cyano, nitro, carbamoyl, esterified carboxy, lower alkanoyl, aroyl or disubstituted carbamoyl; provided that when R'.sub.2 is a group represented by the formula: ##STR2## wherein Y' and Z' are each cyano, nitro, carbamoyl or esterified carboxy, R'.sub.1 is ar(lower) alkyl having substituent(s) selected from the group of lower alkoxy, halogen, nitro and cyano. A process for the protection of amino and/or imino groups in compounds containing them by reacting them with the aforementioned esters is also disclosed.

  公式中的碳酸酯基团R'.sub.1 OCOOR'.sub.2，其中R'.sub.1是较低的烷基，可能具有来自卤素、较低的烷氧基和芳基的基团，或者是芳基-较低烷基，可能具有来自较低烷氧基、卤素、硝基和氰基的基团；R'.sub.2是苯并三唑基，可能具有卤素；或者是由以下公式表示的基团：##STR1## 其中Y'和Z'分别是氰基、硝基、氨基甲酰基、酯化羧基、较低的烷酰基、芳酰基或二取代的氨基甲酰基；但是当R'.sub.2是由以下公式表示的基团时：##STR2## 其中Y'和Z'分别是氰基、硝基、氨基甲酰基或酯化羧基时，R'.sub.1是芳基-较低烷基，具有来自较低烷氧基、卤素、硝基和氰基的基团。还公开了一种通过将含有氨基和/或亚氨基基团的化合物与上述酯反应来保护它们的方法。
• Synthesis of 1-(<i>T</i>-Butoxycarbonyl)benzotriazole and 1-(<i>p</i>-Methoxybenzyloxycarbonyl)benzotriazole and Their Use in the Protection of Amino Acids
  作者：Alan R. Katritzky、Clara N. Fali、Jianqing Li、David J. Ager、Indra Prakash

  DOI：10.1080/00397919708006101

  日期：1997.5

  Abstract Benzotriazol-1-ylcarbonyl chloride, generated from benzotriazole and phosgene, reacts with t-butyl alcohol and p-methoxybenzyl alcohol to give 1-(t-butoxycarbonyl)benzotriazole (4) and 1-(p-methoxy-benzyloxycarbonyl)benzotriazole (5), respectively in good yields. The synthetic utility of reagents 4 and 5 is shown by effective amino protection in phenylalanine and phenylglycine.

  摘要 苯并三唑和光气生成的苯并三唑-1-基碳酰氯与叔丁醇和对甲氧基苄醇反应生成1-（叔丁氧羰基）苯并三唑（4）和1-（对甲氧基-苄氧羰基）苯并三唑（ 5），分别以良好的收益率。苯丙氨酸和苯甘氨酸中的有效氨基保护显示了试剂 4 和 5 的合成效用。
• Oxime carbonates
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04014915A1

  公开（公告）日：1977-03-29

  Novel carbonic acid esters are disclosed which are useful in a process for introducing esterified carboxy-type protective groups on amino and/or imino groups in amino and/or imino group - containing compounds for the temporary protection of said amino and/or imino groups. Additionally, processes for preparing said esters are also disclosed.

  揭示了一种新型的碳酸酯，可用于在氨基和/或亚氨基化合物中引入酯化羧基型保护基的过程，以临时保护所述氨基和/或亚氨基。此外，还揭示了制备所述酯的方法。
• Synthesis of canine motilin, a gastric motor activity-stimulating polypeptide, and its N1-substituted analogs.
  作者：KOUKI KITAGAWA、KUNIO YONETO、SHINYA KIYAMA、KENSHI ANDO、TATSUHIKO KAWAMOTO、TADASHI AKITA、ATSUKO INOUE、TOMIO SEGAWA

  DOI：10.1248/cpb.33.3307

  日期：——

  The docosapeptide corresponding to the entire amino acid sequence of canine motilin, a newly characterized gastric motor activity-stimulating polypeptide, was synthesized by the conventional solution method. All protecting groups employed were removed by 1 M trifluoromethanesulfonic acid-thioanisole-trifluoroacetic acid and the deprotected peptide was purified by gel-filtration on Sephadex G-25, followed by partition chromatography and reverse phase high performance liquid chromatography. When contractile activity on rabbit duodenal muscle was examined, synthetic canine motilin was as active as synthetic porcine motilin. The relative potencies of Lys1 and Ser1 derivatives prepared in the same manner as canine motilin were ca. 1/1000 and 1/250, respectively.

  合成了与犬动脉肽（犬motilin）完整氨基酸序列对应的多肽，这是一种新特征的刺激胃肠运动活性的多肽，使用传统的溶液法合成。所有使用的保护基团均通过1 M三氟甲烷磺酸-硫醚-三氟乙酸去除，去保护的多肽通过Sephadex G-25的凝胶过滤进行纯化，随后进行分配色谱和反相高效液相色谱。在对兔十二指肠肌肉的收缩活性进行检验时，合成的犬动脉肽活性与合成的猪动脉肽相当。以与犬动脉肽相同的方法制备的赖氨酸1和丝氨酸1衍生物的相对效能分别约为1/1000和1/250。
• Papain catalysed esterification of N-protected amino acids
  作者：Shui-Tein Chen、Kung Tsung Wang

  DOI：10.1039/c39880000327

  日期：——

  N-Protected amino acids and amino diacids were converted to their corresponding esters catalysed by immobilized papain with a high concentration of alcohols under mild conditions in a two-phase system.

  在两相系统中，在温和条件下，固定化的木瓜蛋​​白酶与高浓度的醇催化将N保护的氨基酸和氨基二酸转化为相应的酯。