English
往期目录
新闻公告
More
化学进展 2007, Vol. 19 Issue (9): 1357-1370 前一篇   后一篇

• 综述与评论 •

非糖类化合物合成碳环糖*

赵传生 张卫红** 曾弦 冯亚青   

  1. 天津大学化工学院 天津 300072
  • 收稿日期:2006-10-08 修回日期:2006-12-21 出版日期:2007-09-24 发布日期:2007-09-25
  • 通讯作者: 张卫红
下载PDF ( 2022 ) 引用
导出

Carbasugars Synthesis from Non-Carbohydrate Sources

Zhao Chuansheng;Zhang Weihong**;Zeng Xian;Feng Yaqing   

  1. School of Chemical Engineering, Tianjin University, Tianjin 300072,China
  • Received:2006-10-08 Revised:2006-12-21 Online:2007-09-24 Published:2007-09-25
  • Contact: Zhang Weihong
碳环糖是一类呋喃或吡喃糖环中的氧原子被亚甲基取代后形成的糖类似物。碳环糖作为糖类化合物的类似物，和糖类化合物有着不同的活性和稳定性，已经引起了人们的广泛关注。本文综述了从非糖类化合物合成五元及六元碳环糖研究的最新进展。重点介绍了以环二烯基硅烷、奎宁酸、降冰片烯等碳环化合物为原料合成碳环糖的进展。
关键词： 碳环糖, 非糖类化合物, 碳环化合物, 合成
Carbasugars, carbocyclic analogues of true sugars, are compounds in which the ring-oxygen of furanoid or pyranoid sugars is replaced by methylene groupe. As carbohydrate mimics, carbasugars are currently attracting great interest because their reactivity and stability differs enormously from those of carbohydrates. In this paper, recent development in furanoid and pyranoid carbasugars synthesis from non-carbohydrate sources is reviewed. Synthesis with carbocyclic compounds, such as cyclodienylsilane, quinic acid and norbornene etc, as starting materials is discussed in detail.
Key words: carbasugars, non-carbohydrate, carbocyclic compounds, synthesis

中图分类号: 

()

[ 1 ] Suami T. Pure &Appl . Chem. , 1987 , 59 (1) : 1509 —1520
[ 2 ] Compain P , Olivier R. Martin. Bioorg. Med. Chem. , 2001 , 9 :3077 —3092
[ 3 ] Ogawa S. Trends in Glycoscience and Glycotechnology , 2004 , 87 :33 —53
[ 4 ] McCasland G E , Furuta S , DurhamL G. J . Org. Chem. , 1966 ,31 : 1516 —1521
[ 5 ] Wordnigg T M, Sprenger F K F. Mini-Rev. Med. Chem. , 2004 ,4 : 437 —459
[ 6 ] Melo E B , Gomes A D , Carvalho I. Tetrahedron , 2006 , 62 :10277 —10302
[ 7 ] Rajappan V , Scheller SW, Williams SL. Bioorg. Med. Chem. ,2002 , 10 : 883 —886
[ 8 ] Robert J F. Chem. Rev. , 1993 , 93 : 2779 —2831
[ 9 ] Dalko P I , Sinay P. Angew. Chem. Int . Ed. , 1999 , 38 : 773 —777
[10] 陈越磊(Chen Y L) , 岑均达(Cen J D) . 有机化学(Chin. J .Org. Chem. ) , 2004 , 24(11) : 1332 —1139
[11] Angelaud R , Landais Y. J . Org. Chem. , 1996 , 61 : 5202 —5203
[12] Landais Y. Chimia , 1998 , 52 : 104 —108
[13] Angelaud R , Landais Y. Tetrahedron Lett . , 1997 , 38 : 8841 —8844
[14] Angelaud R , Landais Y, Parra-Rapado L. Tetrahedron Lett . ,1997 , 38 : 8845 —8848
[15] Jones G R , Landais Y. Tetrahedron , 1996 , 52 : 7599 —7662
[16] Fleming I. Chemtracts : Org. Chem. , 1996 , 9 : 1 —64
[17] Tmato K. Advances in Silicon Chemistry , 1996 , 3 : 1 —62
[18] Nishimura J , Kawabata J . Tetrahedron , 1969 , 25 : 2461 —2468
[19] Lesimple P , Beau J M, Sinay P. Carbohydr. Res. , 1987 , 171 :289 —300
[20] Landais Y, Parra-Rapado L. Eur. J . Org. Chem. , 2000 , 401 —418
[21] Robertson J , Stafford P M, Bell SJ . J . Org. Chem. , 2005 , 70 :7133 —7148
[22] Shing T K M, Cui Y X, Tang Y. J . Chem. Soc. , Chem.Commun. , 1991 , 756 —757
[23] Shing T K M, Cui Y X, Tang Y. Tetrahedron , 1992 , 48 : 2349 —2358
[24] Shing T K M, Tai V W F. J . Chem. Soc. , Perkin Trans. 1 ,1994 , 2017 —2025
[25] Shing T K M, Tai V W F. J . Chem. Soc. , Chem. Commun. ,1990 , 748 —749
[26] Corey E J , Winter R A E. J . Am. Chem. Soc. , 1963 , 85 :2677 —2678
[27] Bartlett P A , Maitra U , Chouinard P M. J . Am. Chem. Soc. ,1986 , 108 : 8068 —8071
[28] González C , Carballido M, Castedo L. J . Org. Chem. , 2003 ,68 : 2248 —2255
[29] Carballido M, Castedo L , González C. Tetrahedron Lett . , 2001 ,42 : 3973 —3976
[30] Song C J , Jiang S D , Singh G. Synlett , 2001 , 1980 —1985
[31] Kruizinga W H , Strijtveen B , Kellogg R M. J . Org. Chem. ,1981 , 46 : 4324 —4325
[32] Ulibarri A , Nadler W, Skrydstrup T , Audrain H , et al . J . Org.Chem. , 1995 , 60 : 2753 —2761
[33] Murugan A , Yadav A K, Gurjar M K. Tetrahedron Lett . , 2005 ,46 : 6235 —6238
[34] González-Bello C , Castedo L , Caìada F J . Eur. J . Org. Chem. ,2005 , 4 : 1002 —1011
[35] Tian F , Montchamp J L , Frost J W. J . Org. Chem. , 1996 , 61 :7373 —7381
[36] Scholl M, Ding S , Lee C W, Grubbs H. Org. Lett . , 1999 , 1 :953 —956
[37] Zhang Y, Liu A , Ye Z G, et al . Chem. Pharm. Bull . , 2006 , 54(10) : 1459 —1461
[38] Mitsunobu O. Synthesis , 1981 , 1 : 1 —28
[39] Allen J M, Willians J M J . Tetrahedron Lett . , 1996 , 37 : 1859 —1862
[40] Schroder M. Chem. Rev. , 1980 , 80 : 187 —213
[41] Yu S H , Chung S K. Tetrahedron : Asymmetry , 2004 , 15 : 581 —584
[42] Yu S H , Chung S K. Tetrahedron : Asymmetry , 2005 , 16 :2729 —2747
[43] Balani S K, Brannigan I N , Boyd D R , et al . J . Chem. Soc. ,Perkin Trans. 1 , 2001 , 1091 —1097
[44] Kolb H C , Sharpless K B. Tetrahedron , 1992 , 48 : 10515 —10530
[45] Guidot J P , Gall TL. Tetrahedron Lett . , 1993 , 34 : 4647 —4650
[46] Ley S V , Sternfeld F , Taylor S P. Tetrahedron Lett . , 1987 , 28 :225 —226
[47] Ley S V , Sternfeld F. Tetrahedron , 1989 , 45 : 3463 —3476
[48] Ley S V , Parra M, Redgrave AJ , et al . Tetrahedron , 1990 , 46 :4995 —5026
[49] Pingli L , Vandewalle M. Synlett , 1994 , 228 —231
[50] Pingli L , Vandewalle M. Tetrahedron , 1994 , 50 : 7061 —7064
[51] Parker M H , Maryanoff B E , Reitz A B. Synlett , 2004 , 2095 —2098
[52] Boyd D R , Sharma M D , Liamas N M, et al . Org. Biomol .Chem. , 2005 , 3 : 1953 —1963
[53] Humphreys J L , Lowes D J , Wesson K A , et al . Tetrahedron Lett . , 2004 , 45 : 3429 —3432
[54] Carpintero M, Jaramillo C , Femandez2Mayoralas A. Eur. J . Org.Chem. , 2000 , 1285 —1296
[55] Cai S P , Stroud M R , Hakomori S , et al . J . Org. Chem. , 1992 ,57 : 6693 —6696
[56] Takahashi A , Kanbe K, Tamamura T , et al . Anticancer Res. ,1999 , 19 : 3807 —3807
[57] Ogawa S , Asada M, Ooki Y, et al . J . Carbohy. Chem. , 2005 ,677 —683　　　　　　　
[58] Ogawa S , Ohishi Y, Asada M, et al . Org. Biomol . Chem. ,2004 , 2 : 884 —893
[59] Marschner C , Baumgartner J , Griengl H. J . Org. Chem. , 1995 ,50 : 5224 —5235
[60] Mehta G, Mohal N. Tetrahedron Lett . , 1998 , 39 : 3285 —3286
[61] Mehta G, Mohal N. Tetrahedron Lett . , 1998 , 39 : 3281 —3284
[62] Mehta G, Mohal N. Tetrahedron Lett . , 1999 , 40 : 5791 —5794
[63] Mehta G, Mohal N. Tetrahedron Lett . , 1999 , 40 : 5795 —5798
[64] Mehta G, Mohal N. Tetrahedron Lett . , 2000 , 41 : 3505 —3508
[65] Suami T. Top. Curr. Chem. , 1990 , 154 : 257 —283
[66] Suami T , Ogawa S , Nakamoto K, et al . Carbohydr. Res. , 1977 ,58 : 240 —244
[67] Ogawa S , Ara M, Kondoh T , et al . Bull . Chem. Soc. Jpn. ,1980 , 53 : 1121 —1126
[68] Ogawa S , Tsukiboshi Y, Iwasakwa Y, et al . Carbohydr. Res. ,1985 , 136 : 77 —89
[69] Takahashi T , Kotsubo H , Iyobe A , et al . J . Chem. Soc. , Perkin Trans. 1 , 1990 , 3065 —3072
[70] Lemiègre L , Stevens R L , Combret J C , Maddaluno J . Org.Biomol . Chem. , 2005 , 3 : 1308 —1318
[71] Rassu G, Auzzas L , Battistini L , Zanardi F , et al . J . Org.Chem. , 2000 , 65 : 6307 —6318
[72] Rassu G, Auzzas L , Battistini L , et al . J . Org. Chem. , 2001 ,66 : 8070 —8075
[73] Rassu G, Auzzas L , Battistini L , et al . Tetrahedron : Asymmetry ,2003 , 14 : 1665 —1670
[74] Nguyen S T , Gmbbs R H. J . Am. Chem. Soc. , 1993 , 115 :9858 —9859
[75] Chltllder B A. Synlett , 1999 , 267 —267
[76] 李蕊琼(Li R Q) , 傅尧(Fu Y) , 刘磊(Liu L) , 郭庆祥(Guo Q X) . 有机化学(Chin. J . Org. Chem. ) , 2004 , 9 : 1004 —1017
[77] Callam C S , Lowary T L. J . Org. Chem. , 2001 , 66 : 8961 —8972
[78] Choi W J , Moon H R , Kim H O , et al . J . Org. Chem. , 2004 ,69 : 2634 —2636
[79] Lee K, Cass C , Jacobson K A. Org. Lett . , 2001 , 3 : 597 —599
[80] Callam C S , Lowary T L. Org. Lett . , 2000 , 2 : 167 —169
[81] Jeong L S , Lee J A. Antiviral Chem. Chemother. , 2004 , 15(5) :235 —250
[82] Poulsen C S , Madsen R. Synthesis , 2003 , 53 : 1 —19
[83] Dolhem F , Lièvre C , Demailly G. Eur. J . Org. Chem. , 2003 ,12 : 2336 —2342
[84] Diver S T , Giessert A. Chem. Rev. , 2004 , 104 : 1317 —1382
[85] Hansen E C , Lee D. J . Am. Chem. Soc. , 2004 , 126 : 15074 —15080
[86] Xue Z J , Chen P , Peng S Y, et al . Tetrahedron , 2006 , 62 :199 —204
[87] Barlow J S , Dixon D J , Ley S V. J . Chem. Soc. , Perkin Trans.1 , 1999 , 12 : 1627 —1630
[88] Mori M, Sakakibara N , Kinoshita A. J . Org. Chem. , 1998 , 63 :6082 —6083
[1] 何静, 陈佳, 邱洪灯. 中药碳点的合成及其在生物成像和医学治疗方面的应用[J]. 化学进展, 2023, 35(5): 655-682.
[2] 鄢剑锋, 徐进栋, 张瑞影, 周品, 袁耀锋, 李远明. 纳米碳分子——合成化学的魅力[J]. 化学进展, 2023, 35(5): 699-708.
[3] 杨孟蕊, 谢雨欣, 朱敦如. 化学稳定金属有机框架的合成策略[J]. 化学进展, 2023, 35(5): 683-698.
[4] 王新月, 金康. 多肽及蛋白质的化学合成研究[J]. 化学进展, 2023, 35(4): 526-542.
[5] 刘雨菲, 张蜜, 路猛, 兰亚乾. 共价有机框架材料在光催化CO2还原中的应用[J]. 化学进展, 2023, 35(3): 349-359.
[6] 龚智华, 胡莎, 金学平, 余磊, 朱园园, 古双喜. 磷酸酯类前药的合成方法与应用[J]. 化学进展, 2022, 34(9): 1972-1981.
[7] 林业竣, 李艳梅. 翻译后修饰Tau蛋白及其化学全/半合成[J]. 化学进展, 2022, 34(8): 1645-1660.
[8] 宝利军, 危俊吾, 钱杨杨, 王雨佳, 宋文杰, 毕韵梅. 酶响应性线形-树枝状嵌段共聚物的合成、性能及应用[J]. 化学进展, 2022, 34(8): 1723-1733.
[9] 徐鹏, 俞飚. 聚糖化学合成的挑战和可能的凝聚态化学问题[J]. 化学进展, 2022, 34(7): 1548-1553.
[10] 李诗宇, 阴永光, 史建波, 江桂斌. 共价有机框架在水中二价汞吸附去除中的应用[J]. 化学进展, 2022, 34(5): 1017-1025.
[11] 王鹏, 刘欢, 杨妲. 烯烃的氢甲酰化串联反应研究[J]. 化学进展, 2022, 34(5): 1076-1087.
[12] 马晓清. 石墨炔在光催化及光电催化中的应用[J]. 化学进展, 2022, 34(5): 1042-1060.
[13] 赵聪媛, 张静, 陈铮, 李建, 舒烈琳, 纪晓亮. 基于电活性菌群的生物电催化体系的有效构筑及其强化胞外电子传递过程的应用[J]. 化学进展, 2022, 34(2): 397-410.
[14] 闫保有, 李旭飞, 黄维秋, 王鑫雅, 张镇, 朱兵. 氨/醛基金属有机骨架材料合成及其在吸附分离中的应用[J]. 化学进展, 2022, 34(11): 2417-2431.
[15] 杨林颜, 郭宇鹏, 李正甲, 岑洁, 姚楠, 李小年. 钴基费托合成催化剂的表界面性质调控[J]. 化学进展, 2022, 34(10): 2254-2266.
阅读次数
全文


摘要

非糖类化合物合成碳环糖*