(4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazoline | 208935-32-4

• 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: (4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazoline
• 英文别名: (4s,Ss)-4-((t-butyldimethylsilyloxy)methyl)-2-phenyl-5-vinyl-4,5-dihydrooxazole；tert-butyl-[[(4S,5S)-5-ethenyl-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl]methoxy]-dimethylsilane
• CAS: 208935-32-4
• 化学式: C₁₈H₂₇NO₂Si
• 分子量: 317.503
• InChiKey: XYPIZMHFPZHFBE-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazoline 在 palladium on activated charcoal 盐酸 、 9-borabicyclo[3.3.1]nonane dimer 、 氢气 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 D-赤式-二氢-D-鞘氨醇
  参考文献：
  名称：

  Stereoselective synthesis of d-erythro- and l-threo-sphinganines via palladium-catalyzed equilibration and Suzuki coupling

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(02)02309-2
• 作为产物：
  描述：

  N-[(2R)-1-[tert-butyl(dimethyl)silyl]oxy-3-hydroxypropan-2-yl]benzamide 在 四(三苯基膦)钯 potassium carbonate 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 乙腈 为溶剂， 生成 (4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazoline
  参考文献：
  名称：

  全合成肉豆蔻素

  摘要：

  实现了简洁，立体控制的肉豆蔻素合成。关键特征包括钯（0）催化的非对映选择性恶唑啉形成，MgBr 2促进的烯丙基锡的添加以及碘化乙烯与有机锌试剂的钯（0）偶联。

  DOI：

  10.1016/s0040-4039(02)02371-7

文献信息

• Total Synthesis of Sphingofungin F
  作者：Kee-Young Lee、Chang-Young Oh、Won-Hun Ham

  DOI：10.1021/ol020164f

  日期：2002.12.1

  [reaction: see text] A concise, stereocontrolled synthesis of sphingofungin F was achieved. Key features involve diastereoselective oxazoline formation catalyzed by palladium(0), MgBr(2)-promoted gamma-alkoxy allylic stannane addition, and palladium(0)-catalyzed coupling of a vinyl iodide with an organozinc reagent.

  [反应：见正文]精简，立体控制的鞘氨醇单蛋白F的合成得以实现。关键特征包括钯（0）催化的非对映选择性恶唑啉的形成，MgBr（2）促进的γ-烷氧基烯丙基锡的添加以及碘化乙烯与有机锌试剂的钯（0）催化的偶联。
• Stereoselective Allylation of Linear and Chiral β-Amino-α-Hydroxy Aldehydes: Total Syntheses of Tetraacetyl d-lyxo-, d-ribo-, and d-arabino-Phytosphingosines
  作者：In-Soo Myeong、Jin-Seok Kim、Muyng-Gyu Park、Hwan-Hee Jeon、Changyoung Jung、Yong-Taek Lee、Won-Hun Ham

  DOI：10.1055/s-0037-1609343

  日期：2018.5

  involves the chelation between the amido group and aldehyde oxygen by SnCl4, and the Felkin–Anh model by BF3·OEt2. The resulting allylation products were used for the total syntheses of tetraacetyl d-lyxo-, d-ribo-, and d-arabino-phytosphingosines. The stereoselective allylations of β-amino-α-hydroxy aldehydes­ are described. Several Lewis acids (BF3·OEt2, SnCl4, TiCl4, ZnCl2­, and MgBr2·OEt2) were utilized

  摘要 描述了β-氨基-α-羟基醛的立体选择性烯丙基化。在烯丙基化中使用了几种路易斯酸（BF 3 ·OEt 2，SnCl 4，TiCl 4，ZnCl 2和MgBr 2 · OEt 2 ）。SnCl 4介导的抗-β-NHCbz-α-OTBS底物的烯丙基化提供了顺选择性产物，而BF 3 ·OEt 2介导的其烯丙基化则提供了抗选择性产物。的烯丙基化顺通过介导的SnCl-β-NHCbz的制备-α-OTBS 4得到的反-选择性产品。其机理涉及SnCl 4酰胺基与醛氧的螯合，以及BF 3 ·OEt 2的Felkin-Anh模型。将得到的烯丙基化产物用于四乙酰基的总合成d - L-来苏- ， - d -核糖- ，和d -阿拉伯-phytosphingosines。 描述了β-氨基-α-羟基醛的立体选择性烯丙基化。在烯丙基化中使用了几种路易斯酸（BF 3 ·OEt 2，SnCl 4，TiCl 4，ZnCl 2和MgBr
• Palladium-catalyzed formation and stereoselective isomerization of 5-vinyloxazolines. Application to the formal synthesis of (S,S)-4-amino-3-hydroxy-5-phenylpentanoic acid
  作者：Gregory R. Cook、P. Sathya Shanker

  DOI：10.1016/s0040-4039(98)00534-6

  日期：1998.5

  Vinyloxazolidinones have been found to undergo Pd(0)-catalyzed ionization followed by loss of carbon dioxide and subsequent cyclization to form vinyloxazolines. The reaction occurred under mild conditions, and enhancement of diastereomeric ratios with chiral substrates was obtained. 4-Benzyl-5-vinyloxazoline prepared by this method has been utilized in the stereoselective synthesis of (S,S)-4-amino-3-hydroxy-5-phenylpentanoic acid (AHPPA). (C) 1998 Elsevier Science Ltd. All rights reserved.
• Stereoselective synthesis of (+)-spectaline
  作者：Yiu-Suk Lee、Yong-Ho Shin、Yong-Hyun Kim、Kee-Young Lee、Chang-Young Oh、Sung-Jae Pyun、Hyun-Ju Park、Jin-Hyun Jeong、Won-Hun Ham

  DOI：10.1016/s0957-4166(02)00794-2

  日期：2003.1

  Our synthesis of (+)-spectaline revealed that the methodology involving diastereoselective palladium(0)-catalyzed oxazoline formation and intramolecular reductive amination by catalytic hydrogenation of an oxazoline is an effective method for the asymmetric synthesis of natural products possessing complex functionalized piperidine cores. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Total synthesis of myriocin
  作者：Kee-Young Lee、Chang-Young Oh、Yong-Hyun Kim、Jae-Eun Joo、Won-Hun Ham

  DOI：10.1016/s0040-4039(02)02371-7

  日期：2002.12

  A concise, stereocontrolled synthesis of myriocin was achieved. Key features involve diastereoselective oxazoline formation catalyzed by palladium(0), MgBr2-promoted allylic stannane addition, and palladium(0)-catalyzed coupling of a vinyl iodide with an organozinc reagent.

  实现了简洁，立体控制的肉豆蔻素合成。关键特征包括钯（0）催化的非对映选择性恶唑啉形成，MgBr 2促进的烯丙基锡的添加以及碘化乙烯与有机锌试剂的钯（0）偶联。