三-O-乙酰基-D- 葡萄烯糖合成路线 （共 170 条）
反应条件
1: NaOMe / methanol / 5 h / Ambient temperature
2: 1.) (Bu3Sn)2O, 2.) TBABr / 1.) benzene, reflux, 20 h, 2.) benzene, reflux, 17 h
View Scheme
参考文献
Park, Tae Kyo; Kim, In Jong; Hu, Shuanghua; Bilodeau, Mark T.; Randolph, John T.; Kwon, Ohyun; Danishefsky, Samuel J.
Journal of the American Chemical Society, 1996 , vol. 118, # 46 p. 11488 - 11500
反应条件
tetrabutylammomium bromide; water; di(n-butyl)tin oxide; triethylamine
Yield given. Multistep reaction;
参考文献
Kwon, Ohyun; Danishefsky, Samuel J.
Journal of the American Chemical Society, 1998 , vol. 120, # 7 p. 1588 - 1599
反应条件
1.1: NaOMe / methanol
2.1: imidazole
3.1: Bu2SnO
3.2: tetrabutylammonium iodide
4.1: dimethyldioxirane / CH2Cl2; acetone / 0.17 h / 0 °C
4.2: 73 percent / ZnCl2 / CH2Cl2; diethyl ether / 18 h / 20 °C
5.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h
View Scheme
参考文献
Lohman, Gregory J. S.; Seeberger, Peter H.
Journal of Organic Chemistry, 2003 , vol. 68, # 19 p. 7541 - 7543
反应条件
1: 52 percent / acetic acid / palladium acetate / 80 °C
2: 86 percent / hydroxylamine hydrochloride / pyridine / 20 °C
View Scheme
参考文献
Czernecki, S.; Gruy, F.
Tetrahedron Letters, 1981 , vol. 22, p. 437 - 440
反应条件
1: 3,4,6-tri-O-acetyl-D-glucal With sodium azide; ammonium cerium(IV) nitrate in acetonitrile
T=20°C; 24 h;
2: sodium acetate With acetic acid
T=100°C; 2 h;
参考文献
Zhang, Gui-Sheng; Chen, Jie; Min, Ji-Mei; Zhang, Li-He
Helvetica Chimica Acta, 2003 , vol. 86, # 6 p. 2073 - 2081
反应条件
azido chloride in tetrachloromethane
T=0°C; 1 h; Irradiationother halogen-azide, in other solvents under irradiation or in the dark, various time and temperature; Product distribution;
参考文献
Bovin, Nicolai V.; Zurabyan, Sergei E.; Khorlin, Anatoly Y.
Carbohydrate Research, 1981 , vol. 98, p. 25 - 36
反应条件
2: 90 percent / zinc amalgum, anhydrous hydrogen chloride / diethyl ether / 2 h / 0 °C
3: 1.) LiOH; 2.) H2 / 2.) 10percent Pd-C / 1.) DME, 25 deg C, 2 h; 2.) 1 atm, ethylacetate
4: 78 percent / pyridinium dichromate, anhydrous magnesium sulfate, 4A mol.siev. / CH2Cl2 / 1.5 h / 23 °C
6: 1.) potassium isopropoxide; 2.) base / 1.) 0 deg C, 1 h; 2.) hydrolysis
View Scheme
参考文献
Corey, E. J.; Pyne, Stephen G.; Su, Wei-Gou
Tetrahedron Letters, 1983 , vol. 24, # 45 p. 4883 - 4886
反应条件
boron trifluoride diethyl etherate in dichloromethane
1.) -45 deg C, 2.) 0 deg C;
参考文献
Dawe, Robert David; Fraser-Reid, Bert
Journal of Organic Chemistry, 1984 , vol. 49, # 3 p. 522 - 528
反应条件
1: 71 percent / BF3*Et2O / benzene / 0.17 h / 20 °C
2: 48 percent / toluene / 18 h / 85 - 90 °C / Heating
3: 41 percent / BF3*Et2O / CH2Cl2 / 0.25 h
View Scheme
参考文献
De Raadt; Ferrier
Carbohydrate Research, 1991 , vol. 216, p. 93 - 107
反应条件
1: 2.) ZnCl2 / 1.) from 90 to 100 deg C, 10 min, vacuum, 2.) from 140 to 160 deg C, 45 min, vacuum
2: 66.3 percent / sat. methanol. NH3 / 0 °C
View Scheme
参考文献
Sakaguchi, Masakazu; Larroquette, Cynthia A.; Agrawal, Krishna C.
Journal of Medicinal Chemistry, 1983 , vol. 26, # 1 p. 20 - 24
