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化学进展 2006, Vol. 18 Issue (0708): 907-926 前一篇   后一篇

• 综述与评论 •

β-甘露糖苷和β－氨基甘露糖苷的合成

曾佑林1*;孔繁祚2   

  1. 1.湖南师范大学化学化工学院 长沙 410081; 2. 中国科学院生态环境研究中心  北京 100085
  • 收稿日期:2005-09-01 修回日期:2006-02-04 出版日期:2006-08-24 发布日期:2006-08-24
  • 通讯作者: 曾佑林
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Synthesis of β-Mannoside and β-Mannosamine

Youlin Zeng1*;Fanzuo Kong2   

  1. 1. College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, China; 2. Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China
  • Received:2005-09-01 Revised:2006-02-04 Online:2006-08-24 Published:2006-08-24
  • Contact: Youlin Zeng
高立体选择性地合成β－甘露糖苷和β－氨基甘露糖苷是糖化学家所面临的富有挑战性的问题。本文综述了合成β－甘露糖苷和β－氨基甘露糖苷的方法，侧重讨论各种方法在构建β－糖苷键时所具有的优势及其应用。
关键词： β-甘露糖苷, β-氨基甘露糖苷, 分子内糖基配体转移
The synthesis of β-mannoside and β-mannosamine poses one of the greatest challenges to the carbohydrate chemists, because the mechanism of forming mannoside or mannosamine, either neighboring group participation method or non-neighboring group participation method, leads predominately to the α-anomer. Synthetic methods of β-mannoside and β-mannosamine are reviewed in this paper. The superiorities and applications of these methods in constructingβ-glycoside bond are discussed in detail.
Key words: β-mannoside, β-mannosamine, intramolecular aglycon delivery

中图分类号: 

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[ 1 ] Hodgson J . Biotechnology , 1991 , 9 : 609 —613
[ 2 ] Cumming D A. Glycobiology , 1991 , 1 : 115 —130
[ 3 ] Shibahura S KS , Usui T , Kudo T , Tamura A , Gomi S , Ikedu Y,Ikeda D , Takeuchi T. J . Antibiot . , 1993 , 46 : 531 —534
[ 4 ] Fischl M A , Resnick L , Coombs R , Kremer A B , Pottuge J C ,Fass S J , Fife K H , Powderly W G, Collier A C , Aspinall R L ,Smith S L , Kowalski K G, Wallemark C B. J . Acquired Immune Defic. Syndr. , 1994 , 7 : 139 —147
[ 5 ] Ziegler J . J . Natl . Cancer Inst . , 1996 , 88 : 397 —405
[ 6 ] McAuliffe J C , Hindsgaul O. Chem. Ind. (London) , 1997 ,170 —174
[ 7 ] Kobata A. Acc. Chem. Res. , 1993 , 26 : 319 —324
[ 8 ] Dwek R A. Chem. Rev. , 1996 , 96 : 683 —720
[ 9 ] Montreuil J . Adv. Carbohydr. Chem. Biochem. , 1980 , 37 :157 —223
[10] Kornfeld R , Kornfeld S. Annu. Rev. Biochem. , 1985 , 54 :631 —664
[11] Hori T , Sugita M, Ando S , Kuwahara M, Kumauchi K, Sugie E ,Itasaka O. J . Biol . Chem. , 1981 , 256 : 10979 —10985
[12] Takeda T , Hada N , Ogihara Y. Chem. Pharm. Bull . , 1993 ,41 : 2058 —2060
[13] Tatsuta K, Yasuda S. Tetrahedron Lett . , 1996 , 37 : 2453 —2456
[14] Fürstner A , Konetzki I. Tetrahedron , 1996 , 52 : 15071 —15078
[15] Nicolaou K C , van Delft F L , Conley S R , Mitchell H J , Jin Z ,Rodríguez R M. J . Am. Chem. Soc. , 1997 , 119 : 9057 —9058
[16] Zhao Y, Biggins J B , Thorson J S. J . Am. Chem. Soc. , 1998 ,120 : 12986 —12987
[17] Zhao M, Thorson S J . Carbohydr. Res. , 1999 , 319 : 184 —191
[18] Sarbajna S , Misra A K, Roy N. Synth. Commun. , 1998 , 28 :2559 —2561
[19] Lugowski C , Romanowska E. Carbohydr. Res. , 1983 , 118 :173 —181
[20] Nilsson M, Norberg T. J . Chem. Soc. , Perkin Trans. 1 , 1998 ,1699 —1704
[21] Kaji E , Lichtenthaler F W, Osa Y, Takahashi K, Zen S. Bull .Chem. Soc. Jpn. , 1995 , 68 : 2401 —2408
[22] Osa Y, Kaji E , Takahashi K, Hirooka M, Zen S , Lichtenthaler F W. Bull . Chem. Soc. Jpn. , 1994 , 67 : 1130 —1140
[23] Kaji E , Anabuki N , Zen S. Chem. Pharm. Bull . , 1995 , 43 :1441 —1447
[24] Boons G J . Carbohydrate Chemistry. New York : Chapman and Hall , 1998. 10 —14
[25] Barresi F , Hindsgaul O. Front . Nat . Prod. Res. , 1996 , 1 :251 —276
[26] Paulsen H. Angew. Chem. Int . Ed. Engl . , 1982 , 21 : 155 —197
[27] Paulsen H. Angew. Chem. Int . Ed. Engl . , 1990 , 29 : 823 —938
[28] Veeneman G H. Carbohydrate Chemistry. New York : Chapman and Hall , 1998. 149 —156
[29] Kaji E , Lichtenthaler F W. Trends Glycosci . Glycotechnol . ,1993 , 5 : 121 —142
[30] Banoub J . Chem. Rev. , 1992 , 92 : 1167 —1195
[31] Danishefsky S J , Bilodeau M T. Angew. Chem. Int . Ed. Engl . ,1996 , 35 : 1380 —1419
[32] Toshima K, Tatsuta K. Chem. Rev. , 1993 , 93 : 1503 —1531
[33] Boons G J . Contemp. Org. Synth. , 1996 , 173 —201
[34] Garegg P. J . Acc. Chem. Res. , 1992 , 25 : 575 —580
[35] Shimizu M, Togo H , Yokoyama M. Synthesis , 1998 , 799 —822
[36] Gridley J J , Osborn H M I. J . Chem. Soc. , Perkin Trans. 1 ,2000 , 1471 —1491
[37] Jung K H , Müller M, Schmidt R R. Chem. Rev. , 2000 , 100 :4423 —4442
[38] Veeneman G H. Carbohydrate Chemistry. New York : Chapman and Hall , 1998. 161 —165
[39] Grice P , Ley S V , Pietruszka J , Osborn H M I , Priepke H W M,Warriner S L. Chem. A Eur. J . , 1997 , 3 : 431 —440
[40] Matsuo I , Nakahara Y, Ito Y, Nukada T , Nakahara Y, Ogawa T.Bioorg. Med. Chem. , 1995 , 3 : 1455 —1463
[41] Jain R K, Matta K L. Carbohydr. Res. , 1996 , 282 : 101 —111
[42] Kerékgyárto J , van der Ven J G M, Kamerling J P , Lipták A ,Vliegenthart J F G. Carbohydr. Res. , 1993 , 238 : 135 —145
[43] Liu K K C , Danishefsky S J . J . Org. Chem. , 1994 , 59 : 1892 —1894
[44] Danishefsky S J , Hu S , Cirillo P F , Eckhardt M, Seeberger P H.Eur. J . Chem. , 1997 , 3 : 1617 —1628
[45] Lichtenthaler F W, Schneider-Adams T. J . Org. Chem. , 1994 ,59 : 6728 —6934
[46] Nitz M, Purse B W, Bundle D R. Org. Lett . , 2000 , 2 : 2939 —2942
[47] Nitz M, Bundle D R. J . Org. Chem. , 2001 , 66 : 8411 —8423
[48] Osa Y, Kaji E , Takahashi K, Hirooka M, Zen S , Lichtenthaler F W. Chem. Lett . , 1993 , 1567 —1570
[49] Kaji E , Lichtenthaler F W. J . Carbohydr. Chem. , 1995 , 14 :791 —803
[50] Banaszek A , Karpiesiuk W. Carbohydr. Res. , 1994 , 251 :233 —242
[51] Cipolla L , Lay L , Nicotra F. J . Org. Chem. , 1997 , 62 : 6678 —6681
[52] Sato K, Yoshitomo A. Chem. Lett . , 1995 , 39 —40
[53] Sato K I , Yoshitomo A , Takai Y. Bull . Chem. Soc. Jpn. ,1997 , 70 : 885 —890
[54] Matsuo I , Isomura M, Walton R , Ajisaka K. Tetrahedron Lett . ,1996 , 37 : 8795 —8798
[55] Weiler S , Schmidt R R. Tetrahedron Lett . , 1998 , 39 : 2299 —2302
[56] Unverzagt C. Angew. Chem. Int . Ed. Engl . , 1994 , 33 : 1102 —1104
[57] Seifert J , Unverzagt C. Tetrahedron Lett . , 1996 , 37 : 6527 —6530
[58] Barresi F , Hindsgaul O. J . Am. Chem. Soc. , 1991 , 113 :9376 —9377
[59] Barresi F , Hindsgaul O. Synlett . , 1992 , 759 —761
[60] Barresi F , Hindsgaul O. Can. J . Chem. , 1994 , 72 : 1447 —1465
[61] Ennis S C , Fairbanks A J , Tennant-Eyles R J , Yates H S.Synlett , 1999 , 1387 —1390
[62] Seward C M P , Cumpstey I , Aloui M, Ennis S C , Redgrave AJ ,Fairbanks A J . J . Chem. Soc. , Chem. Commun. , 2000 ,1409 —1410
[63] Ennis S C , Fairbanks A J , Tennant-Eyles R J , Yates H S.Tetrahedron , 2001 , 57 : 4221 —4230
[64] Cimpstey I , Fairbanks AJ , Redgrave A. J . Organic Lett . , 2001 ,3 : 2371 —2374
[65] Ito Y, Ogawa T. Angew. Chem. , 1994 , 106 : 1843 —1845 ;Angew. Chem. Int . Ed. Engl . , 1994 , 33 : 1765 —1767
[66] Ito Y, Ohnishi Y, Ogawa T , Nakahara Y. Synlett , 1998 , 1102 —1104
[67] Lergenmüller M, Nukada T , Kuramochi K, Dan A , Ogawa T , Ito Y. Eur. J . Org. Chem. , 1999 , 1367 —1376
[68] Dan A , Ito Y, Ogawa T. Tetrahedron Lett . , 1995 , 36 : 7487 —7490
[69] Dan A , Ito Y, Ogawa T. J . Org. Chem. , 1995 , 60 : 4680 —4681
[70] Dan A , Lergenmüller M, Amano M, Nakahara Y, Ogawa T , Ito Y. Chem. Eur. J . , 1998 , 4 : 2182 —2190
[71] Dan A , Ito Y, Ogawa T. Carbohydr. Lett . , 1996 , 1 : 469 —474
[72] Ito Y, Ogawa T. J . Am. Chem. Soc. , 1997 , 119 : 5562 —5566
[73] Stork G, Kim G. J . Am. Chem. Soc. , 1992 , 114 : 1087 —1088
[74] Stork G, La Clair J J . J . Am. Chem. Soc. , 1996 , 118 : 247 —248
[75] Ziegler T , Lemanski G, Rakoczy A. Tetrahedron Lett . , 1995 ,36 : 8973 —8976
[76] Ziegler T , Lemanski G. Angew. Chem. , 1998 , 110 : 3367 —3369
[77] Ziegler T , Lemanski G. Angew. Chem. Int . Ed. Engl . , 1998 ,37 : 3129 —3132
[78] Ziegler T , Lemanski G. Tetrahedron , 2000 , 56 : 563 —579
[79] Ziegler T , Lemanski G. Eur. J . Org. Chem. , 2000 , 181 —186
[80] Abdel-Rahman A A , El Ashry E H , Schmidt R R. Carbohydr.Res. , 2002 , 337 : 195 —206
[81] Tennant-Eyles R J , Davis B G, Fairbanks J A. J . Chem. Soc. ,Chem. Commun. , 1999 , 1037 —1038
[82] Tennant-Eyles R J , Davis B G, Fairbanks J A. Tetrahedron :Asymmetry , 2003 , 14 : 1201 —1210
[83] Chung S , Park K. Tetrahedron Lett . , 2001 , 42 : 4005 —4007
[84] Crich D , Sun S X. J . Org. Chem. , 1997 , 62 : 1198 —1199
[85] Crich D , Sun S X. J . Am. Chem. Soc. , 1997 , 119 : 11217 —11223
[86] Crich D , Sun S X. J . Am. Chem. Soc. , 1998 , 120 : 435 —436
[87] Crich D , Sun S X. Tetrahedron , 1998 , 54 : 8321 —8348
[88] Crich D , Sun S X. J . Org. Chem. , 1996 , 61 : 4506 —4507
[89] Crich D , Li H M. J . Org. Chem. , 2000 , 65 : 801 —805
[90] Crich D , Li H M, Yao Q J , Wink D J , Sommer R D , Rheingold A L. J . Am. Chem. Soc. , 2001 , 123 : 5826 —5828
[91] Dudkin V Y, Miller J S , Danishefsky S J . Tetrahedron Lett . ,2003 , 44 : 1791 —1793
[92] Crich D , Smith M. J . Am. Chem. Soc. , 2002 , 124 : 8867 —8869
[93] Kim K S , KimJ H , Lee YJ , Lee YJ , Park J . J . Am. Chem.Soc. , 2001 , 123 : 8477 —8481
[94] Usui T , Suzuki M, Sato T , Kawagishi H , Adachi K, Sano H ,Glycoconjugate J . , 1994 , 11 : 105 —110
[95] Vic G, Hastings J J , Crout D H G. Tetrahedron : Asymmetry ,1996 , 7 : 1973 —1984
[96] Taubken N , ThiemJ . Glycoconjugate J . , 1998 , 15 : 757 —767
[97] Wong C H , Halcomb R L , Ichikawa Y, Kajimoto T. Angew.Chem. Int . Ed. Engl . , 1995 , 34 : 412 —432
[98] Ferreira-Dias S , Correia A C , Baptista F O , Fonseca M M R.4 th International Symposium on Biocatalysis and Biotransformations. Giardini Naxos2Taomina , Italia , 1999. 179
[99] Sing S , Scigelova M, Crout D H G. Chem. Commun. , 1996 ,993 —994
[100] Sing S , Scigelova M, Crout D H G. J . Chem. Soc. , Perkin Trans. 1 , 1999 , 777 —782
[101] Watt G M, Revers L , Webberley M C , Wilson I B H , Flitsch S L. Angew. Chem. Int . Ed. Engl . , 1997 , 36 : 2354 —2356
[102] Watt GM, Revers L , Webberley M C , Wilson I B H , Flitsch S L. Carbohydr. Res. , 1998 , 305 : 533 —541
[103] Watt G M, Revers L , Bill R M, Wilson I B H , Flitsch S L.Biochem. Biophys. Acta , 1999 , 1428 : 88 —89
[104] Crich D , Sun S , Bruckova J . J . Org. Chem. , 1996 , 61 : 605 —615
[105] Crich D , Hwang J T , Yuan H. J . Org. Chem. , 1996 , 61 :6189 —6198
[106] Yamazaki N , Eichenberger E , Curran D P. Tetrahedron Lett . ,1994 , 35 : 6623 —6626
[107] Hodosi G, Kováˇc P. J . Am. Chem. Soc. , 1997 , 119 : 2335 —2336
[108] Hodosi G, Kováˇc P. Carbohydr. Res. , 1998 , 308 : 63 —75
[109] Kim W S , Sasai H , Shibasaki M. Tetrahedron Lett . , 1996 , 37 :7797 —7800
[110] Kim W S , Hosono S , Sasai H , Shibasaki M. Heterocycles , 1996 ,42 : 795 —809
[111] Kim W S , Hosono S , Sasai H , Shibasaki M. J . Org. Chem. ,1995 , 60 : 4 —5
[112] Toshima K, Kasumi K I , Matsumura S. Synlett , 1998 , 643 —645
[113] Plante O J , Andrade R B , Seeberger P H. Org. Lett . , 1999 , 1 :211 —214
[114] Hashimoto S , Honda T , Ikegami S. J . Chem. Soc. , Chem.Commun. , 1989 , 11 : 685 —687
[115] Plante O J , Palmacci E R , Seeberger P H. Org. Lett . , 2000 , 2 :3841 —3843
[116] Nagai H , Matsumura S , Toshima K. Carbohydr. Res. , 2003 ,338 : 1531 —1534
[117] Abdel-Rahman A A H , Jonke S , El Ashry E S H , Schmidt R R.Angew. Chem. Int . Ed. Engl . , 2004 , 43 : 4389 —4389
[118] Sasaki A , Ishimizu T , Geyer R , Hase S. FEBS J . , 2005 , 272 :1660 —1668
[119] Matsuo I , Wada M, Manabe S , Yamaguchi Y, Otake K, Kato K,Ito Y. J . Am. Chem. Soc. , 2003 , 125 : 3402 —3403
[120] Codée J D C , Hossain L H , Seeberger P H. Org. Lett . , 2005 ,7 : 3251 —3254
[121] Fürstner A , Konetzki I. Tetrahedron Lett . , 1998 , 39 : 5721 —5724
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