(3S,4S)-methyl 3-hydroxy-6-methyl-4-t-butoxycarbonylamino-heptanoate | 81277-37-4

• 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: (3S,4S)-methyl 3-hydroxy-6-methyl-4-t-butoxycarbonylamino-heptanoate
• 英文别名: (3S,4S)-Methyl 4-<(tert-butoxycarbonyl)amino>-3-hydroxy-6-methylheptanoate；(3S,4S)-N-Boc-statine methyl ester；(3S,4S)-N-(t-butoxycarbonyl)statine methyl ester；N-(Benzyloxycarbonyl)statine methyl ester；methyl (3S,4S)-4-<(tert-butoxycarbonyl)amino>-3-hydroxy-6-methylheptanoate；methyl (3S,4S)-4-<(tert-butoxycarbonyl)amino>-3-hydroxy-6-methylpentanoate；Methyl (3S,4S)-4-tert.-butoxycarbonylamino-3-hydroxy-6-methylheptanoate；(3S,4S)-statine；methyl (3S,4S)-3-hydroxy-6-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]heptanoate
• CAS: 81277-37-4
• 化学式: C₁₄H₂₇NO₅
• 分子量: 289.372
• InChiKey: NLQUWNNPIAQVJY-QWRGUYRKSA-N

物化性质

• 沸点：
  409.0±35.0 °C(predicted)
• 密度：
  1.055±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (3S,4S)-methyl 3-hydroxy-6-methyl-4-t-butoxycarbonylamino-heptanoate 在 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.58h， 生成 methyl (4S,5S)-(4-isobutyl-2-oxo-oxazolidin-5-yl)acetate
  参考文献：
  名称：

  Dufour, Marie-Noelle; Jouin, Patrick; Poncet, Joel, Journal of the Chemical Society. Perkin transactions I, 1986, p. 1895 - 1900

  摘要：

  DOI：
• 作为产物：
  描述：

  叔-丁基氯甲酸酯 在 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 二丁基锡烷 作用下， 生成 (3S,4S)-methyl 3-hydroxy-6-methyl-4-t-butoxycarbonylamino-heptanoate
  参考文献：
  名称：

  Stereoselective intramolecular radical addition of polyhaloacetyl functions to 2-oxazolones. A facile synthesis of statine and its 2,2,-dichloro and 2,2-difluoro analogs

  摘要：

  Intramolecular Ru(II)-catalyzed cyclization of 3-[[(1S,2R)-2-[(polyhaloacetoxy)ethoxy]-1-apocam-phanyl]carbonyl]-2-oxazolones results in the exclusive formation of the 12-membered cycloadducts with complete diastereoselectivity, thus providing a new synthetic route to enantiomerically pure statine analogues including dichloro and difluoro derivatives.

  DOI：

  10.1021/jo00060a006

文献信息

• Sterically Congested Chiral N-Acetyl 2-Oxazolidinone as Acetyl Enolate Equivalents in Stereoselective Aldol Reactions.
  作者：Keiko OTSUKA、Tadao ISHIZUKA、Koreichi KIMURA、Takehisa KUNIEDA

  DOI：10.1248/cpb.42.748

  日期：——

  Sterically constrained and highly congested N-acetyl-DMAOx (1a) serves well as a useful chiral acetyl enolate equivalent which permits a diastereoselective and direct approach to 'acetate' aldols (2) including statine derivative.

  立体位阻受限且高度拥挤的N-乙酰-DMAOx（1a）是一种有用的手性乙酰烯醇等效物，它能够实现对映选择性和直接合成含有丝氨酸衍生物的'乙酸酯'醛醇（2）。
• Asymmetric Synthesis via Acetal Templates. 14.1 Preparation of Enantiomerically Pure (3S,4S)- and (3S,4R)-Statine Derivatives
  作者：R.G. Andrew、R.E. Conrow、J.D. Elliott、W.S. Johnson、S. Ramezani

  DOI：10.1016/s0040-4039(00)96906-5

  日期：——

  Several (3S,4S)- and (3S,4R)-statine derivatives have been prepared by attack of nucleophiles on crystalline, epimeric N-BOC-lactams 7a and 7b. The key step in the synthesis of the lactams was the TiCl4-catalyzed coupling reactions of acetals derived from (R)-1,3-butanediol with allyltrimethylsilane.

  通过亲核试剂攻击结晶的差向异构N-BOC-内酰胺7a和7b，已经制备了几种（3S，4S）-和（3S，4R）-Statine衍生物。内酰胺合成的关键步骤是TiCl 4催化的由（R）-1,3-丁二醇衍生的缩醛与烯丙基三甲基硅烷的偶联反应。
• Chiral synthons for 2-amino alcohols. Facile preparation of optically active amino hydroxy acids of biological interest.
  作者：Tadao Ishizuka、Seigo Ishibuchi、Takehisa Kunieda

  DOI：10.1016/s0040-4020(01)80540-8

  日期：1993.2

  promising method for the versatile synthesis of chiral 2-amino alcohols is provided by the enantioselective functionalization of the olefinic moiety of the simple heterocycle, 2-oxazolone, involving a stereodefined introduction of easily replaceable groups followed by stepwise substitution. Versatility of this method is shown in chiral synthesis of unusual hydroxy amino acids such as statine and hydroxyglutamic

  通过简单杂环2-恶唑酮的烯烃部分的对映选择性官能化，涉及立体定义的易替换基团的引入，然后逐步取代，为手性2-氨基醇的通用合成提供了一种有前途的方法。这种方法的多功能性在不寻常的羟基氨基酸（例如他汀和羟基谷氨酸）的手性合成中得到了证明，它们是生物活性肽的关键成分。
• Process for the stereospecific synthesis of optically pure
  申请人：Sanofi, S.A. and Institut National de la Sante et de la Recherche

  公开号：US04978759A1

  公开（公告）日：1990-12-18

  The process described makes it possible to obtain optically pure 4-amino-3-hydroxycarboxylic acids by means of a series of stereoselective steps. The starting material is an alpha-amino acid in the L or D configuration, with which Meldrum's acid is reacted. The resulting pyrrolone derivative is reduced prior to opening of the pyrrolidine ring. The invention also relates to the new products obtained by the said process and to the pyrrolone derivatives obtained as intermediates.

  所描述的过程通过一系列立体选择性步骤使得获得光学纯的4-氨基-3-羟基羧酸成为可能。起始材料是具有L或D构型的α-氨基酸，与Meldrum's酸反应。在打开吡咯烷环之前，所得的吡咯酮衍生物被还原。该发明还涉及所述过程获得的新产品以及作为中间体所得的吡咯酮衍生物。
• Lewis acid-promoted direct substitution of 4-methoxy- and 4-phenylthio-2-oxazolidinones by alkyl cuprates. Facile preparation of (3s,4s)-statine and (3s,4s)-cyclohexylstatine.
  作者：Seigo Ishibuchi、Yumi Ikematsu、Tadao Ishizuka、Takehisa Kunieda

  DOI：10.1016/0040-4039(91)80822-n

  日期：1991.7

  Treatment of 4-methoxy- and 4-phenylthio-2-oxazolidinones with a combination of cuprates and BF3 results in smooth formation of 4-alkyl and 4-aryl derivatives in high yield. By this method, the titled compounds of biological interest are readily synthesized from (4S,5S)-5-allyl-4-methoxy (or 4-phenylthio)-2-oxazolidinones stereoselectively.