(S)-2-Amino-3-benzyloxy-propionic acid allyl ester | 204992-99-4

• 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: (S)-2-Amino-3-benzyloxy-propionic acid allyl ester
• 英文别名: prop-2-enyl (2S)-2-amino-3-phenylmethoxypropanoate
• CAS: 204992-99-4
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: ZHVZVBIWTBELGH-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-Amino-3-benzyloxy-propionic acid allyl ester 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (S)-3-Benzyloxy-2-(2-tert-butoxycarbonylamino-ethylamino)-propionic acid allyl ester
  参考文献：
  名称：

  Haaima, Gerald; Lohse, Anders; Buchardt, Ole, Angewandte Chemie, 1996, vol. 108, # 17, p. 2068 - 2070

  摘要：

  DOI：
• 作为产物：
  描述：

  N-Boc-O-Bn-L-Ser allyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以98%的产率得到(S)-2-Amino-3-benzyloxy-propionic acid allyl ester
  参考文献：
  名称：

  A macrolactonization approach to the stevastelins

  摘要：

  A synthesis of the stevastelins. a novel class of immunosuppressant agents, is reported based on a macrolactonization approach. This synthesis commenced with the stereoselective preparation of the stearic acid segment from tetradecanal using Evans asymmetric synthesis methodology and an aldol reaction with a thioester. After a high yielding coupling reaction between the fatty acid residue and the corresponding tripeptide. we proceeded with the macrolactonization key step. Thus, macrolactonizations of hydroxy acid 27 and dihydroxy acid 30, according to Yamaguchi conditions, afforded the corresponding 13-membered ring stevastelin derivatives 28 and 31 in 90 and 82% yields, respectively. In this latter case, the corresponding 15-membered lactone was not formed. Finally. depsipeptide derivative 31 was converted into stevastelin C3 (5). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00416-1

文献信息

• Convergent Synthesis of <i>N</i>-Linked Glycopeptides on a Solid Support
  作者：J. Y. Roberge、X. Beebe、S. J. Danishefsky

  DOI：10.1021/ja9740071

  日期：1998.4.1

  Oligosaccharides and glycopeptides are of considerable importance in molecular biology and pharmacology. However, their synthesis is complicated by the large number of different linking sites between each saccharide unit, the need for stereochemical control, the chemical sensitivity of the glycopeptide bonds, and the need to harmonize diverse protecting groups. Here, an efficient solid-phase synthesis of three

  寡糖和糖肽在分子生物学和药理学中具有相当重要的意义。然而，由于每个糖单元之间有大量不同的连接位点、需要立体化学控制、糖肽键的化学敏感性以及协调不同保护基团的需要，它们的合成变得复杂。在这里，提出了一种基于糖组装的三种 N 连接糖肽的有效固相合成。肽域可以扩展，而整体保持与聚合物结合。这里合成的糖肽是迄今为止通过溶液或固相合成获得的最大的 N 连接糖肽之一。
• Haaima, Gerald; Lohse, Anders; Buchardt, Ole, Angewandte Chemie, 1996, vol. 108, # 17, p. 2068 - 2070
  作者：Haaima, Gerald、Lohse, Anders、Buchardt, Ole、Nielsen, Peter E.

  DOI：——

  日期：——
• A macrolactonization approach to the stevastelins
  作者：Francisco Sarabia、Samy Chammaa、F.Jorge López-Herrera

  DOI：10.1016/s0040-4039(02)00416-1

  日期：2002.4

  A synthesis of the stevastelins. a novel class of immunosuppressant agents, is reported based on a macrolactonization approach. This synthesis commenced with the stereoselective preparation of the stearic acid segment from tetradecanal using Evans asymmetric synthesis methodology and an aldol reaction with a thioester. After a high yielding coupling reaction between the fatty acid residue and the corresponding tripeptide. we proceeded with the macrolactonization key step. Thus, macrolactonizations of hydroxy acid 27 and dihydroxy acid 30, according to Yamaguchi conditions, afforded the corresponding 13-membered ring stevastelin derivatives 28 and 31 in 90 and 82% yields, respectively. In this latter case, the corresponding 15-membered lactone was not formed. Finally. depsipeptide derivative 31 was converted into stevastelin C3 (5). (C) 2002 Elsevier Science Ltd. All rights reserved.