methyl (2S,3S)-3-(benzamido)-2-hydroxy-4-phenylbutanoate | 647852-26-4

• 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: methyl (2S,3S)-3-(benzamido)-2-hydroxy-4-phenylbutanoate
• 英文别名: methyl (2S,3S)-3-benzamido-2-hydroxy-4-phenylbutanoate
• CAS: 647852-26-4
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: VCQRVASTFNKEIM-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S)-3-(benzamido)-2-hydroxy-4-phenylbutanoate 在 盐酸 、 氯化亚砜 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 methyl (2R,3S)-3-benzoylamino-2-hydroxy-4-phenylbutanoate
  参考文献：
  名称：

  A practical diastereoselective synthesis of β-amino-α-hydroxy carboxylates

  摘要：

  Practical synthetic routes to beta-amino-alpha-hydroxy carboxylates (AHC) have been developed from amino acids. Reduction of beta-amino-alpha-keto esters 6 with NaBH4 was found to give anti-AHCs 7 in high de, which were efficiently converted to the corresponding syn-AHCs 8 via oxazolidine ring 10 formation. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.009
• 作为产物：
  描述：

  methyl N-trityl-(S)-phenylalaninate 在 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 sodium hydride 、 碳酸氢钠 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 methyl (2S,3S)-3-(benzamido)-2-hydroxy-4-phenylbutanoate
  参考文献：
  名称：

  A practical diastereoselective synthesis of β-amino-α-hydroxy carboxylates

  摘要：

  Practical synthetic routes to beta-amino-alpha-hydroxy carboxylates (AHC) have been developed from amino acids. Reduction of beta-amino-alpha-keto esters 6 with NaBH4 was found to give anti-AHCs 7 in high de, which were efficiently converted to the corresponding syn-AHCs 8 via oxazolidine ring 10 formation. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.009

文献信息

• Efficient Enantioselective Synthesis of α-Hydroxy-β-amino Acids Using the Claisen and Curtius Rearrangements
  作者：Sukbok Chang、Yong Hae Kim、Doo Young Jung、Sol Kang

  DOI：10.1055/s-2005-922793

  日期：——

  Highly enantioselective and facile synthesis of α-hydroxy-β-amino acids has been achieved using the Claisen and Curtius rearrangements as key reactions. Chiral allylic alcohols were employed, which can be prepared by asymmetric catalysis in both E- and Z-forms; both anti- and syn-α-hydroxy-β-amino acids have been synthesized.

  使用 Claisen 和 Curtius 重排作为关键反应已经实现了 α-羟基-β-氨基酸的高度对映选择性和简便合成。采用手性烯丙醇，可通过不对称催化制备E-和Z-型；已经合成了抗和顺-α-羟基-β-氨基酸。
• Diastereoselective Approach to an HIV Protease Inhibitor Intermediate Using a Cation-Exchange Resin Mediated Mannich-Type Reaction
  作者：Makoto Shimizu、Yukinori Hayashi、Ryosuke Hamanaka、Iwao Hachiya

  DOI：10.3987/com-07-s(u)25

  日期：——

  Mannich-type reaction of ketene silyl acetals with a chiral imine proceeded smoothly to give beta-amino esters in good yields with high diasetereoselectivity under the influence of a cation-exchange resin, and the subsequent functional group transformations gave an HIV protease inhibitor intermediate.