(2R,3R)-(+)-ethyl 2-azido-3-isopropyl-3-hydroxypropionate | 159990-09-7

• 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: (2R,3R)-(+)-ethyl 2-azido-3-isopropyl-3-hydroxypropionate
• 英文别名: ethyl (2R,3R)-2-azido-3-hydroxy-4-methylpentanoate
• CAS: 159990-09-7
• 化学式: C₈H₁₅N₃O₃
• 分子量: 201.225
• InChiKey: DCWJURKUJJALOW-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-(+)-ethyl 2-azido-3-isopropyl-3-hydroxypropionate 在 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V) 、 lithium hydroxide monohydrate 、 5%-palladium/activated carbon 、 水 、 氢气 、 N,N-二异丙基乙胺 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Design, synthesis, and evaluation, derivatives of the fat-accumulation inhibitor ternatin: toward ternatin molecular probes

  摘要：

  Ternatin, a cyclic heptapeptide derived from mushroom, strongly inhibits fat accumulation in 3T3-L1 adipocytes. However, its mechanism of action remains unclear. In this Letter, we designed, synthesized, and evaluated its derivatives for use as molecular probes to isolate its target protein. Finally, we successfully established a pair of ternatin molecular probes. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.036
• 作为产物：
  描述：

  4-甲基戊-2-烯酸乙酯 在 氯化亚砜 、 sodium azide 、 甲基磺酰胺 、 AD-mix β 作用下， 以 四氯化碳 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 87.0h， 生成 (2R,3R)-(+)-ethyl 2-azido-3-isopropyl-3-hydroxypropionate
  参考文献：
  名称：

  Design, synthesis, and evaluation, derivatives of the fat-accumulation inhibitor ternatin: toward ternatin molecular probes

  摘要：

  Ternatin, a cyclic heptapeptide derived from mushroom, strongly inhibits fat accumulation in 3T3-L1 adipocytes. However, its mechanism of action remains unclear. In this Letter, we designed, synthesized, and evaluated its derivatives for use as molecular probes to isolate its target protein. Finally, we successfully established a pair of ternatin molecular probes. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.036

文献信息

• Total synthesis of padanamides A and B
  作者：Bohua Long、Shoubin Tang、Ligong Chen、Shiwei Qu、Bo Chen、Junyang Liu、Anita R. Maguire、Zhuo Wang、Yuqing Liu、Hui Zhang、Zhengshuang Xu、Tao Ye

  DOI：10.1039/c3cc00178d

  日期：——

  The first total syntheses of padanamides A and B have been achieved, unambiguously confirming their structures.

  首次完成了padanamides A和B的全合成，明确确认了它们的结构。
• Convergent synthesis and in vivo inhibitory effect on fat accumulation of (−)-ternatin, a highly N-methylated cyclic peptide
  作者：Kenichiro Shimokawa、Kaoru Yamada、Masaki Kita、Daisuke Uemura

  DOI：10.1016/j.bmcl.2007.06.015

  日期：2007.8

  (-)-Ternatin (1), a highly N-methylated cyclic heptapeptide, is a potent inhibitor of fat accumulation against 3T3-LI murine adipocytes (EC50 = 0.14 mu g/mL) [Shimokawa, K.; Mashima, I.; Asai, A.; Yamada, K.; Kita, M.; Uemura, D. Tetrahedron Lett. 2006, 47, 4445]. Compound 1 was synthesized from Boc-protected amino acids in solution. Upon treatment with 1 at 5 mg/kg/day, increases in body weight and fat accumulation in high-fat-fied mice were both significantly suppressed. 0 2007 Elsevier Ltd. All rights reserved.

  (−)-Ternatin (1) 是一种高度N-甲基化的环状七肽，是针对 3T3-LI 小鼠脂肪细胞的强效脂肪积累抑制剂（EC50 = 0.14 μg/mL）[Shimokawa, K.; Mashima, I.; Asai, A.; Yamada, K.; Kita, M.; Uemura, D. Tetrahedron Lett. 2006, 47, 4445]。化合物 1 通过 Boc 保护的氨基酸在溶液中合成。在高脂饮食小鼠中，每天给予 5 mg/kg 的化合物 1 处理后，体重增加和脂肪积累均显著受到抑制。2007 Elsevier 有限公司。版权所有。
• A practical new asymmetric synthesis of (2S,3S)- and (2R,3R)-3-hydroxyleucine
  作者：Karl J. Hale、Soraya Manaviazar、Vern M. Delisser

  DOI：10.1016/s0040-4020(01)85384-9

  日期：1994.1
• (−)-Ternatin, a highly N-methylated cyclic heptapeptide that inhibits fat accumulation: structure and synthesis
  作者：Kenichiro Shimokawa、Itsuka Mashima、Akiko Asai、Kaoru Yamada、Masaki Kita、Daisuke Uemura

  DOI：10.1016/j.tetlet.2006.04.073

  日期：2006.6

  A highly N-methylated cyclic heptapeptide, (-)-ternatin, was isolated from the mushroom Coriolus versicolor, which significantly suppressed fat accumulation against 3T3-L1 triurine adipocytes (EC50 = 0.14 mu g/mL). Although ternatin was previously reported to be antibacterial or antimicrobial compound, its inhibitory effect on fat accumulation has been first shown. The structure of (-)-ternatin was revised to be a cyclo [D-allo-Ile(1)-L-(NMe)Ala(2)-L-(NMe)Leu(3)-L-Leu(4)-L-(NMe)Ala(5)-D-(NMe)Ala(6)-(2R,3R)-3-hydroxy-Leu(7)] by spectroscopic analysis and chemical synthesis. (c) 2006 Elsevier Ltd. All rights reserved.
• CYCLIC HEPTAPEPTIDE AND USE OF THE SAME
  申请人：National University Corporation Nagoya University

  公开号：EP2194062B1

  公开（公告）日：2013-03-13