期刊文献+
任意字段
题名或关键词
题名
关键词
文摘
作者
第一作者
机构
刊名
分类号
参考文献
作者简介
基金资助
栏目信息

含氨基14员环内酰胺类化合物的合成 被引量：1

Synthesis of 14-member macrolactam containing amine
下载PDF
导出
摘要 以烯丙基甘氨酸为原料,通过氨基保护、酰胺化、成环、烯键还原同时脱保护等步骤合成含氨基14员环内酰胺化合物,总收率41.7%,所有化合物的结构均经核磁共振谱(NMR)、质谱(ESI-MS)等方法确证,本合成法可推广至类似大环化合物的合成. Applying allylglycine as starting material, 14-member macrolactam has been synthesized via multiple-step reactions including protection, amidation, ring-closing mctathesis, reduction of carbon- carbon double bond together with deprotection. The overall yield reaches 41.7%. The structures of all products were confirmed by NMR and ESI-MS. The method described here may extend to the synthesis of other similar macrolactams.
作者 王果 翟好真 陈河如
机构地区 暨南大学药学院中药及天然药物研究所 江南大学化学与材料工程学院 暨南大学广东省中药药效物质基础及创新药物研究重点实验室
出处 《暨南大学学报（自然科学与医学版）》 CAS CSCD 北大核心 2012年第1期69-71,共3页 Journal of Jinan University(Natural Science & Medicine Edition)
基金 广东省科技计划项目(No.2010A030100006) 国家自然科学基金(No.81172982)
关键词 大环内酰胺 关环复分解反应 有机合成 macrolactam ring-closing metathesis organic synthesis
分类号 R914.5 [医药卫生—药物化学]
  • 相关文献

参考文献9

  • 1白东鲁,卜运新.形成大环内酰胺方法的进展[J].有机化学,1991,11(2):132-142. 被引量：5
  • 2PIRRUNG M C,BISWAS G,IBARRA-RIVERA T R.Total synthesis of syringolin A and B[J].Org.Lett.,2010,12(10):2402-2405.
  • 3YANG S X,GAO J M,ZHANG A L,et al.Sannastatin,a novel toxic macrolactam polyketide glycoside producedby actinomycete Streptomyces sannanensis[J].BioorgMed Chem Lett,2011,21(13):3905-3908.
  • 4PEREIRA A R,CAO Z,ENGENE N,et al.PalmyrolideA,an unusually stabilized neuroactive macrolide frompalmyra atoll cyanobacteria[J].Org.Lett.,2010,12(20):4490-4493.
  • 5CANOVA S,LEPINE R,THYS A,et al.Synthesis andbiological properties of macrolactam analogs of the naturalproduct macrolide(-)-A26771B[J].Bioorg MedChem Lett,2011,21(16):4768-4772.
  • 6IWASHITA M,FUJII S,ITO S,et al.Efficient and di-versity-oriented total synthesis of Riccardin C and applica-tion to develop novel macrolactam derivatives[J].Tetra-hedron,2011,67(33):6073-6082.
  • 7HARMROLFS K,BRUENJES M,DRAEGER G,et al.Cyclization of synthetic seco-proansamitocins to ansamito-cin macrolactams by actinosynnema pretiosum as biocata-lyst[J].ChemBioChem,2010,11(18):2517-2520.
  • 8朱杰,张学景,邹永.关环复分解反应(RCM)及其催化剂研究进展[J].有机化学,2004,24(2):127-139. 被引量：16
  • 9HASSAN H M A.Recent applications of ring-closing me-tathesis in the synthesis of lactams and macrolactams[J].Chem Commun.,2010,46(48):9100-9106.

二级参考文献65

  • 1[1]Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O′Regan, M. J. Am. Chem. Soc. 1990, 112, 3875.
  • 2[2]Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856.
  • 3[3]Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039.
  • 4[4](a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036.(b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
  • 5[5]Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
  • 6[6]Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
  • 7[7]Hérisson, J. L.; Chauvin, Y. Makromol. Chem. 1970, 141, 161.
  • 8[8]Villemin, D. Tetrahedron Lett. 1980, 21, 1715.
  • 9[9]Tsuji, J.; Hashiguchi, S. Tetrahedron Lett. 1980, 21, 2955.
  • 10[10]Couturier, J. L.; Paillet, C.; Leconte, M.; Basset, J. M.; Weiss, K. Angew. Chem., Int. Ed. Engl. 1992, 31, 628.

共引文献19

同被引文献22

  • 1王卫国,杨明,李佩华,沈树宝.多肽合成中氨基酸活化酯的制备研究[J].化学试剂,2007,29(7):391-393. 被引量：2
  • 2Mhidia R, Boll E, Fcourt F, et al. Exploration of an imide capture/N, N- acyl shift sequence for asparaglne native peptide bond formation [ J ]. Bioorganic & medicinal chemistry, 2013, 21 (12) : 3479 - 3485.
  • 3Lenman M M, Lewis A, Gani D. Synthesis of fused 1,2,5 -triazepine - 1, 5 - diones and some N2 - and N3 - substituted derivatives: potential conformational mimetics for cis - peptidyl prolinamidesl [ J ]. Journal of the Chemical Society, Perkin Transactions 1, 1997 (16) : 2297 -2312.
  • 4Jung S, Tsukuda Y, Kawashima R, et al. Convenient synthesis of acetaminophen analogues containing ot - amino acids and fatty acids via their mixed carbonic carboxylic anhydrides in aqueous organic solvent [J]. Tetrahedron Letters, 2013, 54(42): 5718-5720.
  • 5Michel Brnnel J, Salmi C, Letourneux Y. Efficient peptide coupling method of conjugated carboxylic acids with methyl ester amino acids hydrochloride. Application to the synthesis of Fa - Met, an important enzymatic substrate[ J]. Tetrahedron letters, 2005,46 (2) : 217 -220.
  • 6Hpeg - Jensen T, Jakobsen M H, Holm A. A new method for rapid solution synthesis of shorter peptides by use of PyBOP [ J ]. Tetrahedren Letters, 1991,32 (44) : 6387 - 6390.
  • 7Coste J, Frret E, Jouin P, et al. Oxybenzotriazole free peptide coupling reagents for N - methylated amino acids [ J ]. Tetrahedron letters,1991,32 ( 17 ) : 1967 - 1970.
  • 8Caste J, Freret E, Jouin P. Coupling N - methylated amino acids using PyBroP and PyCloP halogenophosphonium salts: mechanism and fields of application [ J ]. The Journal of Organic Chemistry', 1994,59(9) :2437 - 2446.
  • 9Albericio F, Cases M, Alsina J, et al. On the use of PyAOP, a phosphonium salt derived from HOAt,in solid - phase peptide synthesis [ J ]. Tetrahedron letters, 1997, 38 (27) :4853 - 4856.
  • 10Saito K,Wada T. 3 - Nitro - 1,2,4 - triazol - 1 - yl - tris ( pyrrelidin - 1-y l) pbosphonium hexafluorophosphate (PyNTP) as a condensing reagent for solid - phase peptide synthesis [ J ]. Tetrahedren Letters, 2014.

引证文献1

二级引证文献2

暨南大学学报（自然科学与医学版）
2012年 第1期

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部