(2S,3S)-2-amino-1-(tert-butyldimethylsiloxy)-N-<(tert-butyloxy)carbonyl>-3-hydroxy-4-pentene | 134210-26-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,3S)-2-amino-1-(tert-butyldimethylsiloxy)-N-<(tert-butyloxy)carbonyl>-3-hydroxy-4-pentene
• 英文别名: 1-(tert-butyldimethylsilyloxy)-(2S)-(N-tert-butyloxycarbonyl)amino-4-penten-(3S)-ol；(3S,4S)-5-(t-butyldimethylsilyloxy)-4-(t-butoxycarbonylamino)-3-hydroxypent-1-ene；(2S,3S)-2-amino-1-(tert-butyldimethylsiloxy)-N-[(tert-butyloxy)carbonyl]-3-hydroxy-4-pentene；tert-butyl N-[(2S,3S)-1-[tert-butyl(dimethyl)silyl]oxy-3-hydroxypent-4-en-2-yl]carbamate
• CAS: 134210-26-7
• 化学式: C₁₆H₃₃NO₄Si
• 分子量: 331.528
• InChiKey: NGIPSDYTERGUEU-STQMWFEESA-N

物化性质

• 沸点：
  399.1±42.0 °C(Predicted)
• 密度：
  0.973±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-amino-1-(tert-butyldimethylsiloxy)-N-<(tert-butyloxy)carbonyl>-3-hydroxy-4-pentene 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 (4S,5S)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(2,4,6-trimethyl-benzenesulfonyl)-5-vinyl-oxazolidin-2-one
  参考文献：
  名称：

  A Thermodynamic Preference of Chiral N-Methanesulfonyl and N-Arenesulfonyl 2,3-cis-3-Alkyl-2-Vinylaziridines over Their 2,3-Trans-Isomers:  Useful Palladium(0)-Catalyzed Equilibration Reactions for the Synthesis of (E)-Alkene Dipeptide Isosteres

  摘要：

  Palladium(0)-catalyzed reactions of N-methanesulfonyl- or N-(arenesulfonyl)-3-alkyl-2-vinylaziridines reveal that 2,3-cis-isomers are more stable than the corresponding 2,3-trans-isomers in accord with ab initio calculations. A highly stereoselective synthetic route to (E)-alkene dipeptide isosteres having desired stereochemistries from 2,3-cis-3-isobutyl-2-vinylaziridine by the use of organocopper chemistry is also presented.

  DOI：

  10.1021/jo961760o
• 作为产物：
  描述：

  N-甲氧基-N-甲基-N2-{[(2-甲基-2-丙基)氧基]羰基}-L-丝氨酰胺 在 咪唑 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.34h， 生成 (2S,3S)-2-amino-1-(tert-butyldimethylsiloxy)-N-<(tert-butyloxy)carbonyl>-3-hydroxy-4-pentene
  参考文献：
  名称：

  通过烯烃交叉复分解的多功能合成方法，用于鞘脂和功能化鞘氨醇衍生物。

  摘要：

  通过烯烃交叉复分解反应的两种组合，建立了一种高效且通用的合成各种鞘脂的方法，如鞘磷脂，神经酰胺，鞘氨醇，1-磷酸鞘氨醇和功能化鞘氨醇衍生物。一个反应是在相同的烯烃部分与合适的氨基醇之间，它们从N-Boc-L-丝氨酸开始制备，另一个反应在合适的烯烃与相同的氨基醇之间。[反应：请参见文字]。

  DOI：

  10.1021/ol062258l

文献信息

• Divergent Synthesis of Diastereomeric Sphingosines from a Chiral Aziridine
  作者：On-Yu Kang、Mi-Ri Shin、Han-Young Kang

  DOI：10.1002/bkcs.10830

  日期：2016.7

  an enatiopure form. Aziridine (2) was converted to 3, which was used for the synthesis of 4. Both the advanced key intermediates, vinylaziridines 3 and 4, were successfully converted to threo‐sphingosines 1a and 1b, respectively. Ring‐closing metathesis (RCM) using the Grubbs II catalyst was the key reaction in the synthesis. Two erythro‐sphingosines 1c and 1d were synthesized by the ring‐expansion reactions

  从单一中间体手性氮丙啶（2）开始合成了鞘氨醇的所有四个立体异构体，该中间体通过酶促脱对称化以对映体形式有效制备。氮丙啶（2）转化为3，用于合成4。两种先进的关键中间体乙烯基氮丙啶3和4分别成功地转化为苏式鞘氨醇1a和1b。使用Grubbs II催化剂进行的闭环复分解（RCM）是合成中的关键反应。两个赤型鞘氨醇1c和1d通过乙烯基氮丙啶3和4的扩环反应合成，然后进行RCM反应合成。成功的发散性合成证实，手性乙烯基氮丙啶2可用作合成鞘氨醇相关天然产物的关键中间体。
• Stereoselective synthesis of d-erythro- and l-threo-sphinganines via palladium-catalyzed equilibration and Suzuki coupling
  作者：Gregory R. Cook、Ketheeswaran Pararajasingham

  DOI：10.1016/s0040-4039(02)02309-2

  日期：2002.12

  The Pd-catalyzed isomerization of 5-vinyloxazolines was utilized for the stereoselective synthesis of D-erythro- and L-threo-spinganine triacetate. A hydroboration/Suzuki coupling sequence was employed to elongate the hydrophobic chain. (C) 2002 Elsevier Science Ltd. All rights reserved.
• A highly stereoselective synthesis of (E)-alkene dipeptide isosteres via organocyanocopper-Lewis acid mediation reaction
  作者：Toshiro Ibuka、Hiromu Habashita、Akira Otaka、Nobutaka Fujii、Yusaku Oguchi、Tadao Uyehara、Yoshinori Yamamoto

  DOI：10.1021/jo00014a010

  日期：1991.7

  A stereoselective synthesis of protected (E)-alkene dipeptide isosteres by the reaction of the mesylates of homochiral delta-aminated gamma-hydroxy (E)-alpha,beta-enoates with either RCu(CN)Li.BF3 or RCu(CN)MgX.BF3 reagent is described. The degree of diastereoselectivity has been found to be uniformly high except for the serine- and threonine-derived acetonides 77 and 81. The synthesis permits the introduction of sterically hindered appendages such as isopropyl and tert-butyl groups at the alpha position to the ester group. This methodology provides a new route to a wide range of modified (E)-alkene peptide mimics that may have biological importance.
• Organic Letters 2006, 8, 5569-5572
  作者：

  DOI：——

  日期：——