生物活性糖苷的合成研究
摘要
本论文研究了具有生物活性的糖苷的合成：对位取代苯酚氧糖苷、5-氟尿嘧啶糖苷、腺嘌呤糖苷、黄酮糖苷。
在糖的选择性脱保护中，以氨基葡萄糖盐酸盐为原料，经乙酸酯保护和乙酰基转移两步反应合成了2-乙酰氨基-3，4，6-三-○-乙酰基葡萄糖，该路线是对原有文献的改进和创新。
用三氯乙酰亚胺酸酯法合成了对羟基苯甲酸甲酯葡萄糖苷和对羟基苯乙酮葡萄糖苷。
用直接苷化法，由β-构型的全乙酰化糖合成了5-氟尿嘧啶糖苷和腺嘌呤糖苷。
首次由固—液相转移催化法以溴代四乙酰葡萄糖和7-羟基黄酮为原料以四丁基溴化胺为催化剂合成了葡萄糖、半乳糖、木糖、阿拉伯糖、鼠李糖的7-羟基黄酮苷，其中7-羟基黄酮木糖苷、7-羟基黄酮阿拉伯糖苷和7-羟基黄酮鼠李糖苷是未见文献报道合成过的化合物。
对上述化合物结构进行了质谱、红外、核磁表征。
In this thesis, the synthesis of biological glycosides such as p-substituted phenyl- P -D-glucosides, 5-fuorouracil glycosides, adenine glycosides and 7-hydroxyflavone glycosides were studied.
In the selective deprotection of sugars, a novel method for the synthesis of 2-acetylamino-3,4,6-tri-O-acetyl-2-deoxy-D-glucose from D-glucosamine hydrochloride via acetyl-protection reaction and acetyl-transformation reaction was discribed. It was an improvement of the method of reference.
Two compounds which were O-(4-methoxycarboxyl)phenyl-β-D-glucopyranoside and
O-(4-methylketo)phenyl-β-D-glucopyranoside were synthesized through trichloroacetimidate.
5-Fuorouracil glycosides and adenine glycosides were prepared via β-peracetylglycose.
A series of flavone-7-O-glycosides by reaction of 7-hydroxyflavone and a -D-manose bromide were first synthesized under Bu4NBr as the phase-transfer catalyst.
Their structures were identified by MS, IR and NMR.
在糖的选择性脱保护中，以氨基葡萄糖盐酸盐为原料，经乙酸酯保护和乙酰基转移两步反应合成了2-乙酰氨基-3，4，6-三-○-乙酰基葡萄糖，该路线是对原有文献的改进和创新。
用三氯乙酰亚胺酸酯法合成了对羟基苯甲酸甲酯葡萄糖苷和对羟基苯乙酮葡萄糖苷。
用直接苷化法，由β-构型的全乙酰化糖合成了5-氟尿嘧啶糖苷和腺嘌呤糖苷。
首次由固—液相转移催化法以溴代四乙酰葡萄糖和7-羟基黄酮为原料以四丁基溴化胺为催化剂合成了葡萄糖、半乳糖、木糖、阿拉伯糖、鼠李糖的7-羟基黄酮苷，其中7-羟基黄酮木糖苷、7-羟基黄酮阿拉伯糖苷和7-羟基黄酮鼠李糖苷是未见文献报道合成过的化合物。
对上述化合物结构进行了质谱、红外、核磁表征。
In this thesis, the synthesis of biological glycosides such as p-substituted phenyl- P -D-glucosides, 5-fuorouracil glycosides, adenine glycosides and 7-hydroxyflavone glycosides were studied.
In the selective deprotection of sugars, a novel method for the synthesis of 2-acetylamino-3,4,6-tri-O-acetyl-2-deoxy-D-glucose from D-glucosamine hydrochloride via acetyl-protection reaction and acetyl-transformation reaction was discribed. It was an improvement of the method of reference.
Two compounds which were O-(4-methoxycarboxyl)phenyl-β-D-glucopyranoside and
O-(4-methylketo)phenyl-β-D-glucopyranoside were synthesized through trichloroacetimidate.
5-Fuorouracil glycosides and adenine glycosides were prepared via β-peracetylglycose.
A series of flavone-7-O-glycosides by reaction of 7-hydroxyflavone and a -D-manose bromide were first synthesized under Bu4NBr as the phase-transfer catalyst.
Their structures were identified by MS, IR and NMR.
引文
1 焦克芳，袁越，李松．21世纪药物化学展望：国外医学药学分册，1994，(12)：321-325
2 王克夷，作为信息分子的糖类，化学进展，1996，8(2)：98-108
3 侯宁，徐丽君，新型缩氨基硫脲衍生物-氨基巯三唑Schiff碱的合成与抗菌活性，药学学报，1992，27(10)：738
4 周荣汉，黄沁，药用植物化学分类学，第一版，上海科学技术出版社，1988，53—63
5 Ferrier Robert J, et al. The chemistry of some 1-mercury(Ⅱ) thio-D-glucose compounds: a new synthesis of 1-thio sugars. Carbohydr Res., 1977,57:73
6 Koenigs W.,Konrr E., Ueber einige derivate des traubenzuckers und der galactose. Ber.,1901,34:957-961
7 Mukaiyama T, Murai Y, Shods S, An efficient method for glucosylation of hydroxy compounds using glucopyranosyl fluoride. Chem Lett., 1981:431-432
8 Schmidt R R, Michael J, Facile synthesis of α- and β-O-glycosyl imidates; preparation of glycosides and disaccharides. Angew. Chem. Int. Ed. Engl.,1980,19:731-732
9 West A C,Schuerch C, The reverse anomeric effect and the synthesis of α-glycosides J.Am.Chem.Soc,1973,95:1333-1334
10 Lonn H.,Synthesis of a tri-and a hepta-saccharide which contain α-L-fucopyranosyl groups are part ofthe complex type of carbohydrate moiety of glycopyroteins. Carbohydr.Res., 1985,139:105-113
11 Andesson F., Fugedi P.,Garegg P.J., Synthesis of 1,2-cis-linked glycosides using dimethyl(methylthio)sulfonium triflate as promoter and thioglycosides as glycosyl donors. Tetrahedron Lett., 1986,27:3919-3922
12 Kameyama A., Ishid H., Kiso M. et al.,Total synthesis of sialyl lewis X. Carbohydr. Res., 1991,209:C1-C4
13 Veeneman G. H., Von Boom J.H., An efficient thioglycoside-mediated formation of α-glycosidic linkages promoted by iodonium dicollidine perchlorate. Tetrahedron Lett.,1991,31:275-278
14 Zuurmond H.m., Van der Laan S.C., Van der Marel G.Z.,et al. Iodoniu ion-assisted glycosylation of alkyl(aryl) 1-thioglycosides:regulation of stereoselectivity and reactivity. Carbohydr.Res., 1991,215:C1-C3
15 Marra A., Mallet J.M.,Meyer G. et al., Synlett,1990:572
16 Z Z Yuan, G Magnusson, Carbohydr.Res., 1994,262:79
17 李雯，刘宏民，对位取代苯酚氧甙类化合物的相转移催化合成与结构表征，有机化学，2002，22(12)：1034-1039
18 Demetzos C, Skaltsounis A L,Tillequin F, et al, Phase-transfer-catalyzed synthesis of flavonid glycosides, Carbohydr.Res., 1990,207:131～137
19 Szeja W, Aconverient synthesis of a-D-glucopuranosides, Synthesis, 1988:223～224
20 李润涛，王永富，朱茜，蔡孟深，相转移催化法在糖苷化反应中的应用，化学通报，1999，3：6-11
21 Frieder W. L., Arnold Heerd, Kurt Strobel, Hexuronic Acid and Aminosugar Nucleosides via Stannic Chloride-Catalyzed Glycosidation of Silylpyrimidines with Peracyl-Sugars, Chem.Lett.,1974:449～452
22 Weis Alexander L., Lipitek Inc., L-pyranosyl nucleosides, WO 96/12728
23 Stephen C. M. ,Marcham, Therapeutic Compounds with Pyremidine Base, US5,945,406
24 Joseph Banoub, Paul Boullanger, Dominique Lafont, Synthesis of Oligosaccharides of 2-Amino-2-Deoxy Sugars, Chem.Rev., 1992:1167-1195
25 Nashed M. A., Slife C. W., Kiso M., et al., O-Benzylated Oxazoline Derivatives of 2-Acetamino -2-Deoxy-D-Glucopyranose from 1-Propenyl Glycosides, Carbohydr.Res., 1980, 82:237-252
26 Fraser-Reid V.,WuZ., Udodong U., et al., d.Org.Chem.,1990,55:6068
27 Bilha Fisher, Abraham Nudelman, Margareta Ruse, A novel method for steroselective glucuronidation. J. Org. Chem., 1984,49:4988-4993
28 焦献云，乔梁，王孝伟，核苷研究Ⅱ．苄基糖核苷的立体选择性合成，化学学报，1993，51：1010-1015
29 Srdanka Tomic,Durdica Ljebakovic, Jilka Tomasic, Esterase catalyzed Regioselective hydrolyses of acetylated monosaccharides. Tetrahedron, 1993,49(7): 10977-10986
30 Zhou Fengyan, The synthesis and characterization of 1-Benzyl-3-N-(β-D-glucoside-1-yl)-5-fluorouracil, Hecheng Huaxue ,2001,9(3):272-274
31 江涛，左代姝，管诗华等，含5-氟尿嘧啶的氨基葡萄糖衍生物的制备及抗肿瘤活性研究，Chin Med J, 2001，114(10)：88～93
32 Frieder W.L., Arnold H., Kurt S., Hexuronic acid and aminosugar nucleosides via stannic chloride-catalyzed glycosidations of silyprimidines with peracyl-sugars. Chemistry Lett., 1974: 449-452
33 iedballa U., Vobruggen H., A general synthesis of N-glycosides 6 on the mechanism of the stannic chloride catalyzed silyl Hulbert-Johnson reaction. J. Org. Chem., 1976,41:2084-2086
34 Stephen Martin Courtney, The rapeutic compounds with pyrimddine base. US5, 945, 406
35 Frieder W. L., Peter Voss, Arnold Heerd, Nucleosides X X: Stannic chloride catalyzed. Glycosidations of silylated purines with fully acylated sugars. Tetrahedron Lett., 1974,24:2141-2144
36 闫炳双，孙铁民，武振卿，7-乙酰水杨酰氧基黄酮衍生物的合成，中国药物化学杂志，1994，11：36-40
37 黄涛，有机化学实验，第二版，北京，北京高等教育出版社，1998：176
38 Hough ,Taha, The Reaction of 2-Acetamido-2-deoxy-D-glucose, J. Chem.Soc, 1956:2042-2048
39 Conchie J.,Adbance in carbohydrate chemistry. 1957,12:161-179
40 Jone J.K.N., Perry M.B., Shelton B., et al .,The carbohydrate-protein linkage in glycoproteins. Canadian Jounal of chemistry, 1961,39:1008
41 Graegorz G., Izabela F., Wieslaw S., et al., Chemoselective deprotection of 1-O-acyl sugar derivatives. J.Chem.Res., 1989:152-153
42 Iandor, Garcia-Lopez, Facil regioselective 1-O-deacylation of peracylated copyranoses. Synthesis, 1985:1121-1123
43 Riaz Khan, Paul A.Konowicz, Lucia Gardossi et al., Regioselective deacetylation of fully acetylated mono- and di-saccharides with hydrazine hydrate, Aust, J. Chem., 1996,49:293-298
44 Leabach D.H., Walker P.D., et al., The preparation and properties ofacetochloroglucosamine and its use in the synthesis of 2-acetamido-2-deoxy-β-D-glucosides (N-acetyl-β-D-glucosides ). J.Chem.Soc.,1957:4754～4760
45 Itoh K., Araki Y., Araki Y. Ishido Y. Comprarison of bis(tributyltin) oxide, potassium cyanide, and potassium hydroxide as reagents for the regioselective 1-O-deacetylation of fully acetylated sugars. Carbohydr. Res., 1986,154:165-176
46 Gerhard Grundler, Richard R.Schmidt, Anwendung des triloracetimidat-verfahrens auf 2-azidoglucose-und 2-azidogalactose-derivate. Liebigs Ann. Chem., 1984:1826-1847
47 Katsuya K., Mamoru S., Yoshiaki N., Total synthesis of cerebrosides. Carbohydr. Res. 1978,162:237-246
48 Vijoy J. Patil, A simple acess to trichloroacetimidate. Tetrahedron Lett. 1996,37:1481-1484
49 Julio C.C., Richard R.S., N-tetrachlorophthaloyl-protected trichloracetimidate of glucosamine as glycosyl donor in oligosaccharide synthesis. Tetrahedron Lett., 1995,36:5343-5346
50 Richard R.S., Michel J.Roosm, Direkte synthese von O-α und β-glycosyl-imidaten. Liebigs Ann. Chem., 1984:1343-1357
51 邵颖，汪霞，孔荣祖，熊果苷的合成，江苏化工，1996，24(2)：24
52 孙昌俊，王义贵，李洪祥等，糖苷合成研究(Ⅺ)2—取代氟尿嘧啶β-D-乙酰基木糖苷类化合物的合成及其抗肿瘤活性。中国药物化学杂志，1997，7(2)：84-87
53 孙昌俊，陈再成，张义宁等，5-氟尿嘧啶的β-D-半乳糖苷的合成。有机化学，1992，12：273-277
54 孙昌俊，薛军，王义贵等，5-氟尿嘧啶衍生物的合成及其抗肿瘤活性。中国药物化学杂志，1998，8(2)：91-95
55 孙昌俊，孙义，王义贵等，糖苷合成研究(Ⅶ)—芳磺酰基氟尿嘧啶糖苷的合成及其抗肿瘤活性研究。山东大学学报(自然科学学版)，1997，32(4)：443-447
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57 闫炳双，孙铁民，武振卿，7-乙酰水杨酰氧基黄酮衍生物的合成，中国药物化学杂志，1994，11：36-40
58 徐鲁斌，罗爱民，曹正白，黄酮-4’-O-糖苷的合成，苏州大学学报(自然科学版)，2003，19(2)：95-100
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61 Philip T. Lewis, Kristiina Wahala, Regiospecfic 4'-O-β-D-glucosidation of isoflavones. Tetrahedron Lett., 1998,39:9559-9562
62 Yukiko W., Masao S., Reiko K., Reiko K., Synthesis and biological activity of 4',8-dihydroxyisoflavon-7-yl D-hexopyranosides. Carbohydr. Res., 2001,335:283-289
63 Pericles C., Theofanis G., Marius M., et al., Synthesis of inositol 2-phosphate-quercetin conjugates. Carbohydr. Res., 1996,292:83-90
64 Yu Shao, Yun Long Li, Bing Nan Zhou, Phenolic and triterpenoid glycosides from aster bat angensis. Phytochemistry, 1996,41 (6):1593-1598
65 Aldrich, Catalog handbook of fine chemicals. 1994-1995:792
66 孙昌俊，王义贵，李洪祥等，糖苷合成研究(Ⅵ)1-β-D-(5-取代-2-呋喃甲酸)-糖酯的合成及其抗肿瘤活性。中国药物化学杂志，1996，(3)：162-166
2 王克夷，作为信息分子的糖类，化学进展，1996，8(2)：98-108
3 侯宁，徐丽君，新型缩氨基硫脲衍生物-氨基巯三唑Schiff碱的合成与抗菌活性，药学学报，1992，27(10)：738
4 周荣汉，黄沁，药用植物化学分类学，第一版，上海科学技术出版社，1988，53—63
5 Ferrier Robert J, et al. The chemistry of some 1-mercury(Ⅱ) thio-D-glucose compounds: a new synthesis of 1-thio sugars. Carbohydr Res., 1977,57:73
6 Koenigs W.,Konrr E., Ueber einige derivate des traubenzuckers und der galactose. Ber.,1901,34:957-961
7 Mukaiyama T, Murai Y, Shods S, An efficient method for glucosylation of hydroxy compounds using glucopyranosyl fluoride. Chem Lett., 1981:431-432
8 Schmidt R R, Michael J, Facile synthesis of α- and β-O-glycosyl imidates; preparation of glycosides and disaccharides. Angew. Chem. Int. Ed. Engl.,1980,19:731-732
9 West A C,Schuerch C, The reverse anomeric effect and the synthesis of α-glycosides J.Am.Chem.Soc,1973,95:1333-1334
10 Lonn H.,Synthesis of a tri-and a hepta-saccharide which contain α-L-fucopyranosyl groups are part ofthe complex type of carbohydrate moiety of glycopyroteins. Carbohydr.Res., 1985,139:105-113
11 Andesson F., Fugedi P.,Garegg P.J., Synthesis of 1,2-cis-linked glycosides using dimethyl(methylthio)sulfonium triflate as promoter and thioglycosides as glycosyl donors. Tetrahedron Lett., 1986,27:3919-3922
12 Kameyama A., Ishid H., Kiso M. et al.,Total synthesis of sialyl lewis X. Carbohydr. Res., 1991,209:C1-C4
13 Veeneman G. H., Von Boom J.H., An efficient thioglycoside-mediated formation of α-glycosidic linkages promoted by iodonium dicollidine perchlorate. Tetrahedron Lett.,1991,31:275-278
14 Zuurmond H.m., Van der Laan S.C., Van der Marel G.Z.,et al. Iodoniu ion-assisted glycosylation of alkyl(aryl) 1-thioglycosides:regulation of stereoselectivity and reactivity. Carbohydr.Res., 1991,215:C1-C3
15 Marra A., Mallet J.M.,Meyer G. et al., Synlett,1990:572
16 Z Z Yuan, G Magnusson, Carbohydr.Res., 1994,262:79
17 李雯，刘宏民，对位取代苯酚氧甙类化合物的相转移催化合成与结构表征，有机化学，2002，22(12)：1034-1039
18 Demetzos C, Skaltsounis A L,Tillequin F, et al, Phase-transfer-catalyzed synthesis of flavonid glycosides, Carbohydr.Res., 1990,207:131～137
19 Szeja W, Aconverient synthesis of a-D-glucopuranosides, Synthesis, 1988:223～224
20 李润涛，王永富，朱茜，蔡孟深，相转移催化法在糖苷化反应中的应用，化学通报，1999，3：6-11
21 Frieder W. L., Arnold Heerd, Kurt Strobel, Hexuronic Acid and Aminosugar Nucleosides via Stannic Chloride-Catalyzed Glycosidation of Silylpyrimidines with Peracyl-Sugars, Chem.Lett.,1974:449～452
22 Weis Alexander L., Lipitek Inc., L-pyranosyl nucleosides, WO 96/12728
23 Stephen C. M. ,Marcham, Therapeutic Compounds with Pyremidine Base, US5,945,406
24 Joseph Banoub, Paul Boullanger, Dominique Lafont, Synthesis of Oligosaccharides of 2-Amino-2-Deoxy Sugars, Chem.Rev., 1992:1167-1195
25 Nashed M. A., Slife C. W., Kiso M., et al., O-Benzylated Oxazoline Derivatives of 2-Acetamino -2-Deoxy-D-Glucopyranose from 1-Propenyl Glycosides, Carbohydr.Res., 1980, 82:237-252
26 Fraser-Reid V.,WuZ., Udodong U., et al., d.Org.Chem.,1990,55:6068
27 Bilha Fisher, Abraham Nudelman, Margareta Ruse, A novel method for steroselective glucuronidation. J. Org. Chem., 1984,49:4988-4993
28 焦献云，乔梁，王孝伟，核苷研究Ⅱ．苄基糖核苷的立体选择性合成，化学学报，1993，51：1010-1015
29 Srdanka Tomic,Durdica Ljebakovic, Jilka Tomasic, Esterase catalyzed Regioselective hydrolyses of acetylated monosaccharides. Tetrahedron, 1993,49(7): 10977-10986
30 Zhou Fengyan, The synthesis and characterization of 1-Benzyl-3-N-(β-D-glucoside-1-yl)-5-fluorouracil, Hecheng Huaxue ,2001,9(3):272-274
31 江涛，左代姝，管诗华等，含5-氟尿嘧啶的氨基葡萄糖衍生物的制备及抗肿瘤活性研究，Chin Med J, 2001，114(10)：88～93
32 Frieder W.L., Arnold H., Kurt S., Hexuronic acid and aminosugar nucleosides via stannic chloride-catalyzed glycosidations of silyprimidines with peracyl-sugars. Chemistry Lett., 1974: 449-452
33 iedballa U., Vobruggen H., A general synthesis of N-glycosides 6 on the mechanism of the stannic chloride catalyzed silyl Hulbert-Johnson reaction. J. Org. Chem., 1976,41:2084-2086
34 Stephen Martin Courtney, The rapeutic compounds with pyrimddine base. US5, 945, 406
35 Frieder W. L., Peter Voss, Arnold Heerd, Nucleosides X X: Stannic chloride catalyzed. Glycosidations of silylated purines with fully acylated sugars. Tetrahedron Lett., 1974,24:2141-2144
36 闫炳双，孙铁民，武振卿，7-乙酰水杨酰氧基黄酮衍生物的合成，中国药物化学杂志，1994，11：36-40
37 黄涛，有机化学实验，第二版，北京，北京高等教育出版社，1998：176
38 Hough ,Taha, The Reaction of 2-Acetamido-2-deoxy-D-glucose, J. Chem.Soc, 1956:2042-2048
39 Conchie J.,Adbance in carbohydrate chemistry. 1957,12:161-179
40 Jone J.K.N., Perry M.B., Shelton B., et al .,The carbohydrate-protein linkage in glycoproteins. Canadian Jounal of chemistry, 1961,39:1008
41 Graegorz G., Izabela F., Wieslaw S., et al., Chemoselective deprotection of 1-O-acyl sugar derivatives. J.Chem.Res., 1989:152-153
42 Iandor, Garcia-Lopez, Facil regioselective 1-O-deacylation of peracylated copyranoses. Synthesis, 1985:1121-1123
43 Riaz Khan, Paul A.Konowicz, Lucia Gardossi et al., Regioselective deacetylation of fully acetylated mono- and di-saccharides with hydrazine hydrate, Aust, J. Chem., 1996,49:293-298
44 Leabach D.H., Walker P.D., et al., The preparation and properties ofacetochloroglucosamine and its use in the synthesis of 2-acetamido-2-deoxy-β-D-glucosides (N-acetyl-β-D-glucosides ). J.Chem.Soc.,1957:4754～4760
45 Itoh K., Araki Y., Araki Y. Ishido Y. Comprarison of bis(tributyltin) oxide, potassium cyanide, and potassium hydroxide as reagents for the regioselective 1-O-deacetylation of fully acetylated sugars. Carbohydr. Res., 1986,154:165-176
46 Gerhard Grundler, Richard R.Schmidt, Anwendung des triloracetimidat-verfahrens auf 2-azidoglucose-und 2-azidogalactose-derivate. Liebigs Ann. Chem., 1984:1826-1847
47 Katsuya K., Mamoru S., Yoshiaki N., Total synthesis of cerebrosides. Carbohydr. Res. 1978,162:237-246
48 Vijoy J. Patil, A simple acess to trichloroacetimidate. Tetrahedron Lett. 1996,37:1481-1484
49 Julio C.C., Richard R.S., N-tetrachlorophthaloyl-protected trichloracetimidate of glucosamine as glycosyl donor in oligosaccharide synthesis. Tetrahedron Lett., 1995,36:5343-5346
50 Richard R.S., Michel J.Roosm, Direkte synthese von O-α und β-glycosyl-imidaten. Liebigs Ann. Chem., 1984:1343-1357
51 邵颖，汪霞，孔荣祖，熊果苷的合成，江苏化工，1996，24(2)：24
52 孙昌俊，王义贵，李洪祥等，糖苷合成研究(Ⅺ)2—取代氟尿嘧啶β-D-乙酰基木糖苷类化合物的合成及其抗肿瘤活性。中国药物化学杂志，1997，7(2)：84-87
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