187022-49-7
187022-49-7 結(jié)構(gòu)式
基本信息
苯基3,4,6-三-O-乙?；?2-脫氧-1-硫代-2-(2,2,2-三氯乙氧基甲酰氨基)-Β-D-吡喃葡萄糖苷
苯基 3,4,6-三-O-乙?；?2-脫氧-1-硫代-2-(2,2,2-三氯乙氧基甲酰胺基)-Β-D-吡喃葡萄糖苷
苯基 2-脫氧-1-硫代-2-[[(2,2,2-三氯乙氧基)羰基]氨基]-Β-D-吡喃葡萄糖苷3,4,6-三乙酸酯
苯基 2-脫氧-1-硫代-2-[[(2,2,2-三氯乙氧基)羰基]氨基]-Β-D-吡喃葡萄糖苷3,4,6-三乙酸酯
苯基 3,4,6-三-O-乙酰基-2-脫氧-1-硫代-2-(2,2,2-三氯乙氧基甲酰胺基)-Β-D-吡喃葡萄糖苷
苯基-3,4,6-三-O-乙?；?2-脫氧-1-硫代-2-(2,2,2-三氯乙氧基甲酰氨基)-BETA-D-吡喃葡萄糖苷
(2R,3S,4R,5R,6S)-2-(乙酰氧基甲基)-6-(苯硫基)-5-(((2,2,2-三氯乙氧基)羰基)氨基)四氫-2H-吡喃-3,4-二基二乙酸酯
苯基-3,4,6-三-O-乙?；?2-脫氧-1-硫代-2-(2,2,2-三氯乙氧基甲酰氨基)- Β-D-吡喃葡萄糖苷
PHENYL 3,4,6-TRI-O-ACETYL-2-DEOXY-1-THIO-2-(2,2,2-?TRICHLOROETHOXYFORMA?MIDO)-Β-D-GLUCOPYRANOSIDE苯基 3,4,6-三-O-乙酰基-2-脫氧-1-硫代-2-(2,2,2-三氯乙氧基甲酰胺基)-Β-D-吡喃葡萄糖苷
Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyforMaMido)-β-D-glucopyranoside
Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-β-D-glucopyranoside
Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-β-D-galactopyranoside
Phenyl3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-β-D-glucopyranoside>
Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-beta-D-glucopyranoside
Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-b-D-glucopyranoside, 98%
Phenyl 2-deoxy-1-thio-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-β-D-glucopyranoside 3,4,6-triacetate
物理化學(xué)性質(zhì)
制備方法
108-98-5
![α-D-Glucopyranose, 2-deoxy-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-, 1,3,4,6-tetraacetate](/CAS/20210305/GIF/122210-01-9.gif)
122210-01-9
187022-49-7
一般步驟：將D-葡糖胺鹽酸鹽（20 g，92.8 mmol）溶解于水（250 mL）中，加入飽和NaHCO3水溶液（250 mL）和氯甲酸2,2,2-三氯乙酯（14.05 mL，102 mmol），劇烈攪拌至室溫。反應(yīng)混合物通過燒結(jié)漏斗過濾，收集白色固體并真空干燥過夜。將所得固體溶于吡啶（100 mL）中，冷卻至0℃，緩慢加入乙酸酐（100 mL），隨后加入4-二甲氨基吡啶（DMAP，500 mg，4.1 mmol）。將反應(yīng)液緩慢升溫至室溫并攪拌12小時(shí)。反應(yīng)完成后，用二氯甲烷（200 mL）稀釋反應(yīng)液，依次用1M HCl（3×100 mL）、飽和NaHCO3水溶液（2×100 mL）和鹽水（100 mL）洗滌，有機(jī)相用無水Na2SO4干燥，過濾后減壓濃縮，得到目標(biāo)產(chǎn)物（2R,3S,4R,5R,6S)-2-(乙酰氧基甲基)-6-(苯硫基)-5-(((2,2,2-三氯乙氧基)羰基)氨基)四氫-2H-吡喃-3,4-二基二乙酸酯（葡糖胺11），為白色泡沫狀固體（44.3 g，產(chǎn)率91%）。產(chǎn)物的1H NMR譜（400 MHz，CDCl3）與文獻(xiàn)報(bào)道一致[53]，主要信號(hào)如下：δ 6.23 (1H, d, J = 3.4 Hz), 5.28 (1H, dd, J = 10.7, 9.6 Hz), 5.20 (1H, t, J = 9.8 Hz), 5.14 (1H, d, J = 9.3 Hz, NHTroc), 4.82 (1H, d, J = 12.1 Hz), 4.62 (1H, d, J = 12.1 Hz), 4.28 (1H, dd, J = 12.4, 4.0 Hz), 4.20 (1H, ddd, J = 10.7, 9.4, 3.8 Hz), 4.06 (1H, dd, J = 12.5, 2.4 Hz), 4.06-4.01 (1H, m), 2.20 (3H, s), 2.09 (3H, s), 2.04 (6H, s)。
參考文獻(xiàn)：
[1] Chemical and Pharmaceutical Bulletin, 1997, vol. 45, # 2, p. 312 - 320
[2] Carbohydrate Research, 2017, vol. 452, p. 47 - 53
[3] Journal of Organic Chemistry, 2011, vol. 76, # 10, p. 3691 - 3709
[4] Angewandte Chemie - International Edition, 2014, vol. 53, # 31, p. 8190 - 8194
[5] Angew. Chem., 2014, vol. 126, # 31, p. 8329 - 8333,5