(2S,3R)-Methyl 3-(tert-butoxycarbonylamino)-2-hydroxy-5-methylhexanoate | 73397-32-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3R)-Methyl 3-(tert-butoxycarbonylamino)-2-hydroxy-5-methylhexanoate
• 英文别名: methyl 2-hydroxy-5-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 73397-32-7
• 化学式: C₁₃H₂₅NO₅
• 分子量: 275.345
• InChiKey: XLZZZJSGAZLMIB-UHFFFAOYSA-N

物化性质

• 沸点：
  391.6±32.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 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,3R)-Methyl 3-(tert-butoxycarbonylamino)-2-hydroxy-5-methylhexanoate 在 sodium hydroxide 、 水 、 三氟乙酸 作用下， 生成 (2R,3S)-3-amino-2-hydroxy-5-methylhexanoic acid
  参考文献：
  名称：

  Synthesis of (2S,3R)-3-amino-2-hydroxy-5-methylhexanoic acid derivatives. Application to the synthesis of amastatin, an inhibitor of aminopeptidases

  摘要：

  DOI：

  10.1021/jo01300a004
• 作为产物：
  描述：

  (2R,3S)-2-Benzyloxy-3-tert-butoxycarbonylamino-5-methyl-hexanoic acid methyl ester 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、399.99 kPa 条件下， 以65%的产率得到(2S,3R)-Methyl 3-(tert-butoxycarbonylamino)-2-hydroxy-5-methylhexanoate
  参考文献：
  名称：

  Synthesis of optically active hydroxy amino acids via 2-O-benzylglyceraldehyde N-[(R)-1-phenylethyl]imine

  摘要：

  N-Boc esters of 3-phenylisoserine D, norstatine E, statine F, 'methylsilastatine' G and homostatine H are prepared in 4 to 5 steps from 2-O-benzylglyceraldehyde N-[(R)-1-phenylethyl]imine 1.

  DOI：

  10.1039/cc9960000331

文献信息

• New approaches to the asymmetric synthesis of dipeptide isosteres via β-Lactam Synthon Method
  作者：Iwao Ojima、Hong Wang、Tao Wang、Edward W. Ng

  DOI：10.1016/s0040-4039(97)10677-3

  日期：1998.2

  New and efficient synthetic routes to dipeptide isosteres with high enantiomeric purity, e.g., hydroxyethylene, dihydroxyethylene and hydroxyethylamine isosteres, have been developed via oxiranes 6 and formyloxazolines 13 derived from N-t-Boc-β-lactams 4.

  通过由N -t-Boc-β-内酰胺4衍生的肟基6和甲酰恶唑啉13，已经开发出具有高对映体纯度的二肽等排体（例如，羟乙烯，二羟乙烯和羟乙胺等排体）的新型有效合成途径。
• SHORT CHAIN PEPTIDE INHIBITORS OF HUMAN RENIN
  作者：Rei Matsueda、Yuichiro Yabe、Hiroshi Kogen、Susumu Higashida、Hiroyuki Koike、Yasuteru Iijima、Tatsuo Kokubu、Kunio Hiwada、Eiki Murakami、Yoichi Imamura

  DOI：10.1246/cl.1985.1041

  日期：1985.7.5

  II was found to be important for the design of renin inhibitors. 1-Naphthyl-alanine(Nal(1))-containing tripeptide analogues such as benzyloxycarbonyl-Nal (1)-His-Leucinal (ES-188) and benzyloxycarbonyl-Nal(1)-His-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid (Statine) 2(S)-methylbuthylamid (ES-254) showed high potency and specificity to human renin.

  发现血管紧张素 II C 端序列中的苯丙氨酸残基对于肾素抑制剂的设计很重要。含 1-萘基-丙氨酸 (Nal(1)) 的三肽类似物，例如苄氧羰基-Nal (1)-His-Leucinal (ES-188) 和苄氧羰基-Nal(1)-His-(3S,4S)-4-氨基-3-羟基-6-甲基庚酸 (Statine) 2(S)-methylbutylamide (ES-254) 对人肾素显示出高效力和特异性。
• Synthesis and CD Spectra of Fluoro- and Hydroxy-Substituted -Peptides
  作者：François Gessier、Christian Noti、Magnus Rueping、Dieter Seebach

  DOI：10.1002/hlca.200390150

  日期：2003.6

  as well as the patterns of the CD spectra (Figs. 3–5) depend upon constitution (OH, F, F2 substitution) and configuration (l or u) of the amino acid residues, upon the total number of OH and F substituents in the peptide chain, and upon the solvent used (H2O, MeOH, CF3CH2OH, (CF3)2CHOH). No reliable clues regarding the structures can be obtained from these CD spectra. Only a full NMR analysis will

  β -氨基酸1 - 3与在OH和F的取代基α位上已经制备（方案）从天然（小号） - α -氨基酸的丙氨酸，缬氨酸和亮氨酸，以及掺入到β -hexa-和β -heptapeptides 4 - 12。肽合成是根据常规的溶液策略（Boc / Bn保护）与片段偶联进行的。具有（系列a）和不具有（系列b）的新β肽末端保护以HPLC纯形式分离，并通过NMR光谱和MALDI质谱进行表征。CD光谱的化学性质和谱图（图3-5）取决于OH总数，氨基酸残基的组成（OH，F，F 2取代）和构型（l或u）肽链中的F和F取代基，以及所用溶剂（H 2 O，MeOH，CF 3 CH 2 OH，（CF 3）2 CHOH）上。从这些CD光谱不能获得关于结构的可靠线索。只有一个完整的NMR分析就能回答的问题：一）哪些已知的β肽二级结构（图1和2）与OH和F衍生物相容？b）极性和/或氢键主链取代基是否增强了新的二级结构？此外，
• New renin-inhibitory peptides and their use
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0152255A2

  公开（公告）日：1985-08-21

  Compounds of formula wherein R' represents alkyl having an α-amino or protected α-amino substituent and an aryl, heterocyclic or heterocyclic- dithio substituent; R2 represents a variety of aliphatic and cycloaliphatic hydrocarbon groups, which may be substituted; R3 represents isobutyl, sec-butyl, benzyl or (C3-CS cyclo- elkyl)methyl; and X represents a group of formula -CH(-A-R")-Y) (in which: A represents a single bond or an alkylene group: R4 represents an optionally protected carboxy group, an optionally N-substituted carbamoyl group, an optionally N-substituted carbazoyl group or an acyl group; and Y represents a hydroxy group, a mercapto group or a formyl group), or a group of formula -P(O)(R5)-OH (in which R5 represents an alkyl group having at least one optionally protected carboxy, N-substituted carbamoyl, optionally N-substituted carbazoyl, C2-C7 aliphatic carboxylic acyl or aromatic carboxylic acyl substituent)]; and their salts are renin inhibitors, which may be used in the treatment of angiotensin-induced hypertension.

  式中的化合物 式中 R'代表具有α-氨基或受保护α-氨基取代基的烷基，以及芳基、杂环或杂环-二硫代基； R2 代表各种可被取代的脂肪族和环脂族烃基； R3 代表异丁基、仲丁基、苄基或（C3-CS 环烷基）甲基；以及 X 代表式 -CH(-A-R")-Y)的基团 其中A 代表单键或亚烷基：R4 代表任选受保护的羧基、任选 N-取代的氨基甲酰基、任选 N-取代的咔唑酰基或酰基；Y 代表羟基、巯基或甲酰基），或 式中-P(O)(R5)-OH 的基团 (其中 R5 代表具有至少一个任选保护的羧基、N-取代的氨基甲酰基、任选 N-取代的咔唑酰基、C2-C7 脂肪族羧酰基或芳香族羧酰基取代基的烷基）]；它们的盐类是肾素抑制剂，可用于治疗血管紧张素诱导的高血压。
• Novel inhibitors of hepatitis C NS3–NS4A serine protease derived from 2-aza-bicyclo[2.2.1]heptane-3-carboxylic acid
  作者：Srikanth Venkatraman、F. George Njoroge、Wanli Wu、Viyyoor Girijavallabhan、Andrew J. Prongay、Nancy Butkiewicz、John Pichardo

  DOI：10.1016/j.bmcl.2005.12.046

  日期：2006.3

  Prolonged hepatitis C infection is the leading cause for cirrhosis of the liver and hepatocellular carcinoma. The etiological agent HCV virus codes a single polyprotein of similar to 3000 amino acids that is processed with the help of a serine protease NS3A to produce structural and non-structural proteins required for viral replication. Inhibition of NS3 protease can potentially be used to develop drugs for treatment of HCV infections. Herein, we report the development of a series of novel NS3 serine protease inhibitors derived from 2-aza-bicyclo[2.2.1]-heptane carboxylic acid with potential therapeutic use for treatment of HCV infections. (C) 2005 Elsevier Ltd. All rights reserved.