中文
Announcement
More
Progress in Chemistry 2007, Vol. 19 Issue (9): 1357-1370 Previous Articles   Next Articles

• Review •

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: Revised: Online: Published:
  • Contact: Zhang Weihong
PDF ( 2025 ) Cited
Export

EndNote

Ris

BibTeX

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.

CLC Number: 

[ 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] Jing He, Jia Chen, Hongdeng Qiu. Synthesis of Traditional Chinese Medicines-Derived Carbon Dots for Bioimaging and Therapeutics [J]. Progress in Chemistry, 2023, 35(5): 655-682.
[2] Jianfeng Yan, Jindong Xu, Ruiying Zhang, Pin Zhou, Yaofeng Yuan, Yuanming Li. Nanocarbon Molecules — the Fascination of Synthetic Chemistry [J]. Progress in Chemistry, 2023, 35(5): 699-708.
[3] Xinyue Wang, Kang Jin. Chemical Synthesis of Peptides and Proteins [J]. Progress in Chemistry, 2023, 35(4): 526-542.
[4] Liu Yvfei, Zhang Mi, Lu Meng, Lan Yaqian. Covalent Organic Frameworks for Photocatalytic CO2 Reduction [J]. Progress in Chemistry, 2023, 35(3): 349-359.
[5] Zixuan Liao, Yuhui Wang, Jianping Zheng. Research Advance of Carbon-Dots Based Hydrophilic Room Temperature Phosphorescent Composites [J]. Progress in Chemistry, 2023, 35(2): 263-373.
[6] Yehjun Lim, Yanmei Li. Chemical Synthesis/Semisynthesis of Post-Translational Modified Tau Protein [J]. Progress in Chemistry, 2022, 34(8): 1645-1660.
[7] Peng Xu, Biao Yu. Challenges in Chemical Synthesis of Glycans and the Possible Problems Relevant to Condensed Matter Chemistry [J]. Progress in Chemistry, 2022, 34(7): 1548-1553.
[8] Deshan Zhang, Chenho Tung, Lizhu Wu. Artificial Photosynthesis [J]. Progress in Chemistry, 2022, 34(7): 1590-1599.
[9] Fangyuan Li, Junhao Li, Yujie Wu, Kaixiang Shi, Quanbing Liu, Hongjie Peng. Design and Preparation of Electrode Nanomaterials with “Yolk-Shell”Structure for Lithium/Sodium-Ion/Lithium-Sulfur Batteries [J]. Progress in Chemistry, 2022, 34(6): 1369-1383.
[10] Shiyu Li, Yongguang Yin, Jianbo Shi, Guibin Jiang. Application of Covalent Organic Frameworks in Adsorptive Removal of Divalent Mercury from Water [J]. Progress in Chemistry, 2022, 34(5): 1017-1025.
[11] Xiaoqing Ma. Graphynes for Photocatalytic and Photoelectrochemical Applications [J]. Progress in Chemistry, 2022, 34(5): 1042-1060.
[12] Xiuli Shao, Siqi Wang, Xuan Zhang, Jun Li, Ningning Wang, Zheng Wang, Zhongyong Yuan. Fabrication and Application of MFI Zeolite Nanosheets [J]. Progress in Chemistry, 2022, 34(12): 2651-2666.
[13] Baoyou Yan, Xufei Li, Weiqiu Huang, Xinya Wang, Zhen Zhang, Bing Zhu. Synthesis of Metal-Organic Framework-NH2/CHO and Its Application in Adsorption Separation [J]. Progress in Chemistry, 2022, 34(11): 2417-2431.
[14] Yang Linyan, Guo Yupeng, Li Zhengjia, Cen Jie, Yao Nan, Li Xiaonian. Modulation of Surface and Interface Properties of Cobalt-Based Fischer-Tropsch Synthesis Catalyst [J]. Progress in Chemistry, 2022, 34(10): 2254-2266.
[15] Chenliu Tang, Yunjie Zou, Mingkai Xu, Lan Ling. Photocatalytic Reduction of Carbon Dioxide with Iron Complexes [J]. Progress in Chemistry, 2022, 34(1): 142-154.