10034-20-5

基本信息
2-氨基-2-脫氧-Β-D-吡喃葡萄糖 1,3,4,6-四乙酸酯鹽酸鹽
1,3,4,6-四-O-乙?;?2-氨基-2-脫氧-Β-D-葡萄糖鹽酸鹽
1,3,4,6-Tetra-O-acetyl-a-D-glucosamineHCI
1,3,4,6-Tetra-O-acetyl-2-aMino-2-deoxy-beta-D-gluc
2-Amino-2-deoxy-β-D-glucopyranose 1,3,4,6-tetraacetate
1,3,4,6-Tetra-O-acetyl-beta-D-glucosamine hydrochloride
1,3,4,6-Tetra-O-acetyl-2-amino--D-glucopyranose, Hydrochloride
1,3,4,6-Tetra-o-acetyl-2-aMino-2-deoxy-beta-d-glucopyranose, HCl
2-Amino-2-deoxy-1,3,4,6-tetra-O-acetyl--D-glucopyranose Hydrochloride
1,3,4,6-Tetra-O-acetyl-2-aMino-2-deoxy-b-D-glucopyranose Hydrochloride
b-D-Glucopyranose, 2-aMino-2-deoxy-, 1,3,4,6-tetraacetate, hydrochloride
物理化學(xué)性質(zhì)
制備方法

7597-81-1

5432-46-2
以(2S,3R,4R,5S,6R)-6-(乙酰氧基甲基)-3-(((E)-4-甲氧基亞芐基)氨基)四氫-2H-吡喃-2,4,5-三乙酸三酯(4.0 g, 8.6 mmol)為原料,將其溶解于預(yù)熱的丙酮(36 mL)中。隨后,向溶液中緩慢加入5 M HCl(2 mL),觀察到沉淀生成。將反應(yīng)混合物冷卻至室溫后,加入乙醚(36 mL)并持續(xù)攪拌2小時。通過過濾收集沉淀,用乙醚洗滌,并在減壓下干燥,得到1,3,4,6-四-O-乙?;?2-氨基-2-去氧-D-吡喃葡萄糖鹽酸鹽(2.9 g, 79%)為白色固體。產(chǎn)物的熔點為205°C(文獻(xiàn)值:231-233°C,點燃[49],熔點235°C);比旋光度[α]20D +36.6(c 1.0, MeOH),文獻(xiàn)值[49] +32(H2O);紅外光譜(IR)νmax 2939 cm?1(寬峰,NH3Cl),1751 cm?1(C=O);1H-NMR(DMSO-d6, 300 MHz)δ 1.95(6H, s, CH3CO),2.00(3H, s, CH3CO),2.14(3H, s, CH3CO),3.52(1H, t, J = 9.7 Hz, H-2),3.98(2H, m, H-6, H-5),4.15(1H, dd, J = 12.3, 4.1 Hz, H-6),4.87(1H, t, J = 9.8 Hz, H-4),5.28(1H, t, J = 9.8 Hz, H-3),5.84(1H, d, J = 8.8 Hz, H-1),8.26(3H, s, NH3Cl)。
參考文獻(xiàn):
[1] Journal of Organic Chemistry, 1999, vol. 64, # 16, p. 5926 - 5929
[2] Journal of the American Chemical Society, 2018, vol. 140, # 8, p. 3120 - 3127
[3] Carbohydrate Research, 2010, vol. 345, # 11, p. 1541 - 1547
[4] Advanced Synthesis and Catalysis, 2010, vol. 352, # 14-15, p. 2657 - 2662
[5] RSC Advances, 2014, vol. 4, # 12, p. 6239 - 6245