(S)-2-((2S,3S)-2-Amino-3-benzyloxy-butyrylamino)-3-benzyloxy-propionic acid allyl ester | 452956-85-3

• 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-((2S,3S)-2-Amino-3-benzyloxy-butyrylamino)-3-benzyloxy-propionic acid allyl ester
• 英文别名: prop-2-enyl (2S)-2-[[(2S,3S)-2-amino-3-phenylmethoxybutanoyl]amino]-3-phenylmethoxypropanoate
• CAS: 452956-85-3
• 化学式: C₂₄H₃₀N₂O₅
• 分子量: 426.513
• InChiKey: BJVOBJZRIIMIMA-NYVOZVTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  99.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-((2S,3S)-2-Amino-3-benzyloxy-butyrylamino)-3-benzyloxy-propionic acid allyl ester 在 吗啉 、 四(三苯基膦)钯 、 2,4,6-三氯苯甲酰氯 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.17h， 生成 (3S,6S,9S,12R,13R)-6-(1-Benzyloxy-ethyl)-3-benzyloxymethyl-13-[(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pentadecyl]-9-isopropyl-12-methyl-1-oxa-4,7,10-triaza-cyclotridecane-2,5,8,11-tetraone
  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
• 作为产物：
  描述：

  N-Boc-O-Bn-L-Ser allyl ester 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (S)-2-((2S,3S)-2-Amino-3-benzyloxy-butyrylamino)-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

• 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.