(2S,3R)-2-(2-(benzyloxy)benzamido)-3-hydroxybutanoic acid | 81254-78-6

• 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: (2S,3R)-2-(2-(benzyloxy)benzamido)-3-hydroxybutanoic acid
• 英文别名: L-N-[2-benzyloxy (benzoyl)] threonine；(2S,3R)-3-hydroxy-2-[(2-phenylmethoxybenzoyl)amino]butanoic acid
• CAS: 81254-78-6
• 化学式: C₁₈H₁₉NO₅
• 分子量: 329.353
• InChiKey: URTDGHWNBYTOOS-WBMJQRKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 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：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-(2-(benzyloxy)benzamido)-3-hydroxybutanoic acid 在 氯化亚砜 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (4S,5S)-2-(2-(benzyloxy)phenyl)-N-ethyl-5-methyl-4,5-dihydrooxazole-4-carboxamide
  参考文献：
  名称：

  LANTHANIDE CLUSTERS AND METHODS OF USE THEREOF

  摘要：

  本发明涉及基于苯基-噁唑啉酰胺（POxA）配体的多核镧系手性簇以及其使用方法。本发明的手性簇具有高荧光性能和高稳定性。

  公开号：

  US20160002269A1
• 作为产物：
  描述：

  (2S,3R)-methyl 2-(2-(benzyloxy)benzamido)-3-hydroxybutanoate 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (2S,3R)-2-(2-(benzyloxy)benzamido)-3-hydroxybutanoic acid
  参考文献：
  名称：

  LANTHANIDE CLUSTERS AND METHODS OF USE THEREOF

  摘要：

  本发明涉及基于苯基-噁唑啉酰胺（POxA）配体的多核镧系手性簇以及其使用方法。本发明的手性簇具有高荧光性能和高稳定性。

  公开号：

  US20160002269A1

文献信息

• A Latent Oxazoline Electrophile for N−O−C Bond Formation in Pseudomonine Biosynthesis
  作者：Elizabeth S. Sattely、Christopher T. Walsh

  DOI：10.1021/ja804499r

  日期：2008.9.17

  Nitrogen-heteroatom bonds figure prominently in the structural, chemical, and functional diversity of natural products. In the case of Pseudomonas siderophore pseudomonine, an N-O hydroxamate linkage is found uncommonly configured in an isoxazolidinone ring. In an effort to understand the biogenesis of this heterocycle, we have characterized the pseudomonine synthetase in vitro and reconstituted the complete biosynthetic pathway. Our results indicate that the isoxazolidinone of pseudomonine arises from spontaneous rearrangement of an oxazoline precursor. To the best of our knowledge, this is a previously uncharacterized mode of post-assembly line heterocyclization. Our results establish the oxygen of the ubiquitous siderophore hydroxamate functionality as a nucleophile and may be indicative of general strategy for N-O-C bond formation in nature.
• NOVEL PROCESS FOR THE SYNTHESIS OF EXOCHELINS
  申请人：Keystone Biomedical, Inc.

  公开号：EP1105416A1

  公开（公告）日：2001-06-13
• US6063919A
  申请人：——

  公开号：US6063919A

  公开（公告）日：2000-05-16
• [EN] NOVEL PROCESS FOR THE SYNTHESIS OF EXOCHELINS<br/>[FR] NOUVEAU PROCEDE DE SYNTHESE D'EXOCHELINES
  申请人：KEYSTONE BIOMEDICAL INC

  公开号：WO2000009547A1

  公开（公告）日：2000-02-24

  A process for the synthesis of an Exochelin comprising the steps of generating L-N-[(2-benzyloxy-(benzoyl)]serine or L-N-[2-benzyloxy(benzoyl)] threonine, creating L-N-t-Boc-εhydroxynorleucine and reacting same to produce L-N-Boc-ε-bromonorleucine trimethylsilylethyl ester, providing a dicarboxylic acid and forming an O-benzyl methyl hydroxamate from the dicarboxylic acid, coupling the O-benzyl methyl hydroxamate with the L-N-Boc-ε-bromonorleucine trimethylsilylethyl ester to give an L-N?2-Boc-N6¿-methyl,N6-(benzyloxy) lysine 2-trimethylsilylethyl ester which incorporates the dicarboxylic acid as modified above, removing the N-tert-butoxycarbonyl protecting group from the L-N?2-Boc-N6¿-methyl,N6-(benzyloxy) lysine 2-trimethylsilylethyl ester to yield a substituted lysine, and coupling the same with the L-N-[2-benzyloxy(benzoyl) serine or -threonine to yield a 2-trimethyl silylethyl ester of dibenzyl Exochelic acid, transforming the 2-trimethyl silylethyl ester of dibenzyl Exochelic acid to dibenzyl Exochelic acid , preparing benzyl epi-cobactin, forming an ester bond between the dibenzyl Exochelic acid and benzyl epi-cobactin to form an intermediate, and, hydrogenolytically removing three benzyl groups from said intermediate, resulting in the synthesized Exochelin. More particularly, a synthesis for Exochelin 786SM (R) is disclosed wherein the dicarboxylic acid is suberic acid and the serine form is utilized.