methyl (2S,3R)-3-hydroxy-2,3-diphenylpropanoate | 120851-53-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: methyl (2S,3R)-3-hydroxy-2,3-diphenylpropanoate
• 英文别名: threo-2.3-Diphenyl-3-hydroxypropionsaeure-methylester
• CAS: 120851-53-8
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: DLFSYZUHQWKGDA-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (Z)-1,2-diphenyl-pent-3-en-1-ol 、 重氮甲烷 、 potassium permanganate 生成 methyl (2S,3R)-3-hydroxy-2,3-diphenylpropanoate
  参考文献：
  名称：

  HAYASHI, TAMIO;MATSUMOTO, YONETATSU;KIYOI, TAKAO;ITO, YOSHIHIKO;KOHRA, SH+, TETRAHEDRON LETT., 29,(1988) N 44, C. 5667-5670

  摘要：

  DOI：

文献信息

• Enantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates via boron-mediated asymmetric aldol reaction
  作者：P. Veeraraghavan Ramachandran、Prem B. Chanda

  DOI：10.1039/c3cc40860d

  日期：——

  enantioselective synthesis of anti- and syn-beta-hydroxy-alpha-phenyl carboxylates has been achieved by the proper choice of solvent, temperature, alkoxy group, and amine for the diisopinocampheylboron-mediated asymmetric enolization-aldolization of phenylacetates. The pure diastereomers can be readily separated by column chromatography.

  抗和SYN-β-羟基-α-苯基羧酸酯的试剂控制的，diastereo-和对映选择性合成已经通过溶剂，温度，烷氧基，胺为diisopinocampheylboron介导的非对称的烯醇化-缩醛反应的适当选择来实现苯乙酸酯。可以通过柱色谱法容易地分离纯的非对映异构体。
• Diastereoselective reactions of 1,1′-binaphthyl ester enolates with carbonyl electrophiles
  作者：Mija Ahn、Kiyoshi Tanaka、Kaoru Fuji

  DOI：10.1039/a706673b

  日期：——

  Diastereoselectivity in the aldol and the conjugate additions of 2′-hydroxy-1,1′-binaphthyl ester enolates with a variety of carbonyl electrophiles has been examined. The ester enolate generated by BuLi reacts with several aldehydes to give the threo products preferentially with high diastereoselectivity and in good yield. Satisfactory diastereoselectivity has also been observed in the minor erythro derivatives. A mechanistic interpretation of the results is made on the basis of the absolute stereochemistry of the products.

  已研究了2′-羟基-1,1′-联萘酯酮烯与多种羰基电烯的醇醛反应和结合加成反应中的二面体选择性。由BuLi生成的酯酮烯与几种醛反应，优先生成threo产物，具有高的二面体选择性和良好的收率。在少量的erythro衍生物中也观察到了令人满意的二面体选择性。根据产物的绝对立体化学，对结果进行了机制解释。
• Phosphine Oxide Catalyzed, Tetrachlorosilane-Mediated Enantioselective Direct Aldol Reactions of Thioesters
  作者：Sergio Rossi、Rita Annunziata、Franco Cozzi、Laura Raimondi

  DOI：10.1055/s-0034-1379914

  日期：——

  The stereoselective direct aldol reaction of S-phenyl thioesters and aromatic aldehydes promoted by tetrachlorosilane was realized for the first time; the proposed mechanism involves the formation of a chiral cationic hypervalent silicon species and requires the presence of catalytic amounts of a Lewis base, like a chiral phosphine oxide. The reaction affords syn -hydroxy thioesters as major isomers in good yields, high diastereoselectivity (up to 99:1), and up to 92% enantiomeric excess. The absolute configuration of the major isomer was established by converting the product into the corresponding -hydroxy ester. The scope of the reaction was also investigated by employing differently substituted thioesters in combination with different aromatic aldehydes.
• HAYASHI, TAMIO;MATSUMOTO, YONETATSU;KIYOI, TAKAO;ITO, YOSHIHIKO;KOHRA, SH+, TETRAHEDRON LETT., 29,(1988) N 44, C. 5667-5670
  作者：HAYASHI, TAMIO、MATSUMOTO, YONETATSU、KIYOI, TAKAO、ITO, YOSHIHIKO、KOHRA, SH+

  DOI：——

  日期：——