(RS)-N-<(allyloxy)carbonyl>-α-hydroxyglycine | 92138-25-5

• 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: (RS)-N-<(allyloxy)carbonyl>-α-hydroxyglycine
• 英文别名: α-(hydroxy)-N-(allyloxycarbonyl)glycine；{[(Allyloxy)carbonyl]amino}(hydroxy)acetic acid；2-hydroxy-2-(prop-2-enoxycarbonylamino)acetic acid
• CAS: 92138-25-5
• 化学式: C₆H₉NO₅
• 分子量: 175.141
• InChiKey: UARRSABPEGWDNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (RS)-N-<(allyloxy)carbonyl>-α-hydroxyglycine 在 papain 对甲苯磺酸 作用下， 以 甲醇 、 phosphate buffer 、 正己烷 、 乙腈 、 苯 为溶剂， 反应 30.75h， 生成 Alloc-L-Ncy(Tmob)-OH
  参考文献：
  名称：

  Synthesis of protected norcysteines for SPPS compatible with Fmoc strategy

  摘要：

  We report the synthesis of racemic Alloc-Ncy(Tmob)-OH, the resolution of its methyl ester and demonstrate its application to form a norcystine bridge in octreotide-amide using the Fmoc strategy on solid phase. N-Alloc and S-Tmob protections of norcysteine (Ncy) were found to be a preferred choice for Fmoc strategy over three other protected norcysteines synthesized, that is, Fmoc-Ncy(tBu)-OH, Alloc-Ncy(tBu)-OH, and Alloc-Ncy(Trt)-OH. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.082
• 作为产物：
  描述：

  烯丙基氨基甲酸酯 、 乙醛酸 以 乙醚 为溶剂， 反应 24.0h， 生成 (RS)-N-<(allyloxy)carbonyl>-α-hydroxyglycine
  参考文献：
  名称：

  Synthesis of racemic .alpha.-amino carboxamides via Lewis acid-mediated reactions of .alpha.-methoxyglycinamide derivatives with allylsilanes: enzymic resolution to optically active .alpha.-amino acids

  摘要：

  A short and expedient synthetic route to optically active, saturated and gamma,delta-unsaturated alpha-amino acids is reported. The key step is a BF3.OEt2-mediated reaction of allylsilanes with N-(alkoxycarbonyl)-alpha-methoxyglycinamides 11-15, leading to the corresponding gamma,delta-unsaturated alpha-aminocarboxamides. The genuine S(N)1-character of this process with iminium ion 6 as intermediate is proven in the case of the glycine ester 10. Thus, reaction of enzymatically resolved 10 with pi-nucleophiles leads to racemic products. The most useful iminium precursors are the N-methoxyamides 12-14 providing good yields of coupling products. The most convenient N-protective group is the allyloxycarbonyl group. Deprotection proceeds via a Pd(0)-catalyzed transprotection to the corresponding BOC-protected analogues. Four examples of the enzymatic resolution of alpha-amino carboxamides, by using an L-specific aminopeptidase from Pseudomonas putida, are described in detail. Most notably, secondary N-methoxyamides are good substrates for the enzyme to provide the desired a-amino acids in high optical purity.

  DOI：

  10.1021/jo00051a019

文献信息

• Preparation of 3-benzothienylglycines
  申请人：Eli Lilly and Company

  公开号：US04458085A1

  公开（公告）日：1984-07-03

  3-Benzothienylglycines are prepared by reaction of a benzothiophene with an .alpha.-hydroxyglycine derivative in the presence of trifluoroacetic acid.

  3-苯并噻吩基甘氨酸是在三氟乙酸存在下，通过苯并噻吩与α-羟基甘氨酸衍生物的反应制备而成。
• Benzothienylglycyl cephalosporin derivatives
  申请人：Eli Lilly and Company

  公开号：US04492693A1

  公开（公告）日：1985-01-08

  7-(3-Benzothienyl)glycylamido cephalosporins have good gram positive activity and favorable pharmacokinetics and are orally effective.

  7-(3-苯并噻吩基)甘氨酰头孢菌素具有良好的革兰氏阳性活性和良好的药代动力学特性，并且具有口服有效性。
• Improvements in or relating to the preparation of 3-benzothienylglycines
  申请人：ELI LILLY AND COMPANY

  公开号：EP0122153A1

  公开（公告）日：1984-10-17

  3-Benzothienylglycines are prepared by reaction of a benzothiophene with an a-hydroxyglycine derivative in the presence of trifluoroacetic acid.

  3-苯并噻吩基甘氨酸是由苯并噻吩与 a-羟基甘氨酸衍生物在三氟乙酸存在下反应制备而成。
• Improvements in or relating to benzothienylglycyl cephalosporin derivatives
  申请人：ELI LILLY AND COMPANY

  公开号：EP0122154A2

  公开（公告）日：1984-10-17

  7-(3-Benzothienyl)glycylamido cephalosporins provided by this invention possess favorable pharmacokinetics and are orally-effective against gram positive microorganisms.

  本发明提供的 7-(3-苯并噻吩基)甘氨酰头孢菌素具有良好的药代动力学，对革兰氏阳性微生物具有口服疗效。
• Orally absorbable cephalosporin antibiotics. 1. Structure-activity relationships of benzothienyl- and naphthylglycine derivatives of 7-aminodeacetoxycephalosporanic acid
  作者：Stjepan Kukolja、Susan E. Draheim、Janice L. Pfeil、Robin D. G. Cooper、Bernard J. Graves、Richard E. Holmes、David A. Neel、George W. Huffman、J. Alan Webber

  DOI：10.1021/jm00150a022

  日期：1985.12

  A structure-activity relationship study of a number of orally absorbed cephalosporins together with their syntheses is described. These new cephalosporins are benzothienyl- and naphthylglycine derivatives of 7-aminodeacetoxycephalosporanic acid. Several different synthetic methods for the glycine side chains, their protection, and the final acylations are reported. Several of these analogues were more active than cephalexin both in vitro and in vivo against commonly encountered Gram-positive bacteria. (R)-7-(3-Benzothienylglycylamido)-3-methyl-3-cephem-4-carboxylic acid (1R) has emerged as a potent antibacterial agent and is currently undergoing preclinical evaluation.