(2S,3S)-2-hydroxy-3-(benzyloxycarbonylamino)-4-phenylbutanoic acid methyl ester | 126015-23-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S)-2-hydroxy-3-(benzyloxycarbonylamino)-4-phenylbutanoic acid methyl ester
• 英文别名: (2S,3S)-3-[[(benzyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutanoic acid methyl ester；methyl N-(benzyloxycarbonyl)-(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoate；(2S,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenyl butyric acid methyl ester；methyl (2S,3S)-3-[(benzyloxycarbonyl)amino]-2-hydroxy-4-phenylbutyrate；methyl (2S,3S)-2-hydroxy-4-phenyl-3-(phenylmethoxycarbonylamino)butanoate
• CAS: 126015-23-4
• 化学式: C₁₉H₂₁NO₅
• 分子量: 343.379
• InChiKey: LKDKNFNUPLFYKN-IRXDYDNUSA-N

物化性质

• 沸点：
  532.5±50.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 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,3S)-2-hydroxy-3-(benzyloxycarbonylamino)-4-phenylbutanoic acid methyl ester 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 1-羟基苯并三唑 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 苯基甲基N-[(2S)-4-氨基-1-[[(2S,3S)-4-[(2S)-2-(叔丁基氨基甲酰)吡咯烷-1-基]-3-羟基-4-氧代-1-苯基丁烷-2-基]氨基]-1,4-二氧代丁烷-2-基]氨基甲酸酯
  参考文献：
  名称：

  有趣的结构-活性关系是基于诺斯达汀的肽对HIV蛋白酶的有效抑制作用的基础。

  摘要：

  DOI：

  10.1021/jm00085a020
• 作为产物：
  描述：

  苄基(S)-1-(N-甲氧基-N-甲基氨基甲酰基)-2-苯乙基氨基甲酸酯 在 盐酸 、 lithium aluminium tetrahydride 、 水 作用下， 生成 (2S,3S)-2-hydroxy-3-(benzyloxycarbonylamino)-4-phenylbutanoic acid methyl ester
  参考文献：
  名称：

  Inactivation of serine protease, α-chymotrypsin by fluorinated phenylalanine analogues

  摘要：

  Fluorinated phenylalanine analogues were found to be slow-binding or reversible competitive inhibitors of alpha-chymotrypsin. A series of these compounds were designed to inactivate alpha-chymotrypsin as a result of the formation of hydrogen-bonding between fluorine atom of the inhibitors and the amide protons known as oxy-anion hole in the active-site of serine and cysteine proteases. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00342-3

文献信息

• Acylation of Alkyl Halides and Amino Aldehydes with a Phosphane Oxide-Based d1-Synthon
  作者：Marco Brünjes、Christof Kujat、Holger Monenschein、Andreas Kirschning

  DOI：10.1002/ejoc.200300631

  日期：2004.3

  Alkyl iodides and α-amino aldehydes can be homologated to the corresponding methyl esters and β-amino methyl esters, including β-amino-α-hydroxy methyl esters, using lithiated (dimethoxymethyl)diphenylphosphane oxide. The primary α,α-(dimethoxy)diphenylphosphane oxides obtained by this Horner−Wittig type process collapse to give the target esters under proton-catalyzed conditions in the presence of

  使用锂化（二甲氧基甲基）二苯基膦氧化物，烷基碘和 α-氨基醛可以与相应的甲酯和 β-氨基甲酯（包括 β-氨基-α-羟基甲酯）同系。通过这种 Horner-Wittig 型方法获得的主要 α,α-（二甲氧基）二苯基膦氧化物在质子催化条件下在水存在下崩溃以产生目标酯。详细且仔细进行的机理研究表明，二苯基氧化膦基团被质子化激活，并作为该过程中的初始离去基团。在由氧化膦稳定的阴离子与 α-氨基醛反应衍生的加合物的情况下，可以通过 KOtBu 介导的消除中间体来实现与 β-氨基-和 β-氨基-α-羟基甲酯的同系化O,O-烯酮缩醛。它们可以在酸性条件下与水反应以产生 β-氨基甲酯，或者可以在 Sharpless 不对称二羟基化条件下处理以直接提供 β-氨基-α-羟基甲酯。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Lithiated Dimethoxymethyl Diphenyl Phosphine Oxide, A Versatile Formiate Carbanion Equivalent
  作者：Holger Monenschein、Marco Brünjes、Andreas Kirschning

  DOI：10.1055/s-2002-20486

  日期：——

  Aldehydes are homologated to the corresponding α-hydroxy methyl esters using lithiated dimethoxymethyl diphenyl phosphine oxide. The primary addition product of this Horner-Wittig process collapses to the corresponding α-hydroxy ester under proton-catalyzed conditions.

  使用锂化的二甲氧基甲基二苯基膦氧化物将醛类同系为相应的 α-羟基甲酯。在质子催化条件下，该 Horner-Wittig 过程的主要加成产物分解为相应的 α-羟基酯。
• Tributyltin Cyanide, a Novel Reagent for the Stereoselective Preparation of 3-Amino-2-hydroxy Acids via Cyanohydrin Intermediates
  作者：Rosario Herranz、Julia Castro-Pichel、Teresa García-López

  DOI：10.1055/s-1989-27367

  日期：——

  Reaction of tributyltin cyanide with optically active 2-N-benzyloxyearbonylamino aldehydes 1 gives the corresponding O-tributylstannyl cyanohydrins 2 and 3 stereoselectively. Compounds 2 and 3 are transformed in situ into the methyl 3-N-benzoyloxycarbonyl-amino-2-hydroxy esters 4 and 5, respectively, via the imidate hydrochloride intermediates. Saponification of 4 and 5 provide 3-amino-2-hydroxy acids 6 and 7, respectively, key intermediates in the preparation of Bestatin, Amastatin, and analogues.

  三丁基氰化锡与光学活性2-N-苯甲氧羰基氨基醛1反应立体选择性地得到相应的O-三丁基甲锡烷基氰醇2和3。化合物2和3通过亚氨酸盐酸盐中间体分别原位转化为甲基3-N-苯甲酰氧基羰基-氨基-2-羟基酯4和5。 4和5的皂化分别提供3-氨基-2-羟基酸6和7，它们是制备Bestatin、Amastatin和类似物的关键中间体。
• Stereoselection in the synthesis of threo- and erythro-3-amino-2-hydroxy-4-phenyl-butanoic acid using chiral acetal templates
  作者：Rosario Herranz、Julia Castro-Pichel、Soledad Vinuesa、M. Teresa García-López

  DOI：10.1039/c39890000938

  日期：——

  derived from Z-L- and Z-D-phenyl alaninal, (Z=N-benzyloxycarbonyl), and (+)-(2S,4S)- and (–)-(2R,4R)-2,4-pentanediol stereoselectively gave the four stereoisomers of the 3-amino-2-hydroxy-4-phenylbutanoic acid, key intermediates for bestatin and bestatin analogues.

  三氟化硼-乙醚介导的三甲基甲硅烷基氰化物（TMSCN ）加到衍生自Z- L-和Z- D-苯基丙氨酸，（Z = N-苄氧羰基）和（+）-（2 S，4 S）的手性缩醛中-和（-）-（2 R，4 R）-2,4-戊二醇立体选择得到3-氨基-2-羟基-4-苯基丁酸的四种立体异构体，这是Bestatin和Bestatin类似物的关键中间体。
• Azobenzene-Containing, Peptidyl α-Ketoesters as Photobiological Switches of α-Chymotrypsin
  作者：Andrew J Harvey、Andrew D Abell

  DOI：10.1016/s0040-4020(00)00883-8

  日期：2000.12

  Three photoswitchable, peptidomimetic inhibitors of oc-chymotrypsin have been synthesised. The compounds comprise an azobenzene, an alpha -ketoester and L-phenylalanine. The compounds were photoisomerised to give enriched states of the (E) and (Z) isomers and these states were assayed against alpha -chymotrypsin. The inhibitors were shown to be moderately active with switching ability of between two- and three-fold between the two isomer-enriched states. The behaviour of the inhibitors in solution was examined; specifically, their hydration and configurational stability. (C) 2000 Elsevier Science Ltd. All rights reserved.