81058-27-7 (2,3,4,6-O-四特戊酰基-alpha-D-溴代吡喃葡萄糖,[(2R,3R,4S,5R,6R)-6-bromo-3,4,5-tris[(2,2-dimethylpropanoyl)oxy]oxan-2-yl]methyl 2,2-dimethylpropanoate)

CAS号:
81058-27-7
中文名称:
2,3,4,6-O-四特戊酰基-alpha-D-溴代吡喃葡萄糖
英文名称:
[(2R,3R,4S,5R,6R)-6-bromo-3,4,5-tris[(2,2-dimethylpropanoyl)oxy]oxan-2-yl]methyl 2,2-dimethylpropanoate
分子式:
C26H43BrO9
分子量:
579.518228769302

2,3,4,6-O-四特戊酰基-alpha-D-溴代吡喃葡萄糖(81058-27-7)名称与标识符

名称

中文别名:
2,3,4,6-O-四特戊酰基-alpha-D-溴代吡喃葡萄糖;卡格列净 中间体 KG-2.1;2,3,4,6-四邻叔戊酰基-alpha-d-溴化吡喃葡萄糖;达格列净Dapagliflozin卡格列净Canagliflozin中间体, 2,3,4,6-O-四特戊酰基-alpha-D-溴代吡喃葡萄糖;
英文别名:
2,3,4,6-Tetra-O-pivaloyl-alpha-D-glucopyranosyl bromide;TETRAKIS(2,2-DIMETHYLPROPANOATE)-A-D-GLUCOPYRANOSYL BROMIDE;TETRA-O-PIVALOYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE;2,3,4,6-Tetra-O-pivaloyl-a-D-glucopyranosylbromide;2,3,4,6-Tetra-O-pivaloyl-a-D-glucopyranosyl bromide (stabilised with CaCO3);[(2S,3S,4S,5R,6S)-6-broMo-3,4,5-tris(2,2-diMethylpropanoyloxy)tetrahydropyran-2-yl]Methyl2,2-diMethylpropanoate;(2R,3R,4S,5R,6R)-2-Bromo-6-((pivaloyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate);2,3,4,6-TETRA-O-PIVALOYL-α-D-GLUCOPYRANOSYL BROMIDE;Tetra-O-pivaloyl-α-D;Tetra-O-pivaloyl-α-D-glucopyranosyl Bromide;2,3,3-Trimethyl-5-Chloro-3H-Indole;Tetrakis(2,2-Dimethylpropanoate)-α-D-Glucopyranosyl Bromide;[(2R,3R,4S,5R,6R)-6-bromo-3,4,5-tris[(2,2-dimethylpropanoyl)oxy]oxan-2-yl]methyl 2,2-dimethylpropanoate;(2R,3R,4S,5R,6R)-2-Bromo-6-((pivaloyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyltris(2,2-dimethylpropanoate);F12912;EC 686-241-8;BS-29473;A864609;2,3,4,6-Tetra-O-pivaloyl-alpha-D-glucopyranosyl bromide, >=90% (TLC);AKOS024462364;AC-26309;DTXSID801020960;2,3,4,6-tetra-o-pivaloyl-a-d-glucopyranosyl bromide;2,3,4,6-Tetra-O-pivaloylalpha-D-glucopyranosyl bromide;(2R,3R,4S,5R,6R)-2-Bromo-6-((pivaloyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate) (Empagliflozin Impurity pound(c);[(2R,3R,4S,5R,6R)-6-bromo-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate;alpha-D-Glucopyranosyl bromide, 2,3,4,6-tetrakis(2,2-dimethylpropanoate);2,3,4,6-TETRAKIS-O-(2,2-DIMETHYLPROPANOYL)-ALPHA-D-GLUCOPYRANOSYL BROMIDE;81058-27-7;BSDBCYHGMPHOAL-SFFUCWETSA-N;Tetra-O-pivaloyl-;CS-0165066;MFCD08275217;AMY39015;SCHEMBL1039837;2,3,4,6-tetra-O-pivaloyl-alpha-D-gluco-pyranosyl bromide;(2R,3R,4S,5R,6R)-2-bromo-6-(pivaloyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate);A inverted exclamation mark-D-glucopyranosyl bromide;α-D-Glucopyranosyl bromide, tetrakis(2,2-dimethylpropanoate) (9CI);2,3,4,6-Tetrakis(2,2-dimethylpropanoate) alpha-D-Glucopyranosyl Bromide; 2,3,4,6-Tetra-O-pivaloyl-alpha-D-glucopyranosyl bromide;;I+/--aD-aGlucopyranosyl bromide, 2,a3,a4,a6-atetrakis(2,a2-adimethylpropanoate);

标识符

MDL:
MFCD08275217
InChIKey:
BSDBCYHGMPHOAL-SFFUCWETSA-N
Inchi:
1S/C26H43BrO9/c1-23(2,3)19(28)32-13-14-15(34-20(29)24(4,5)6)16(35-21(30)25(7,8)9)17(18(27)33-14)36-22(31)26(10,11)12/h14-18H,13H2,1-12H3/t14-,15-,16+,17-,18+/m1/s1
SMILES:
O([C@@H]1[C@@H](COC(=O)C(C)(C)C)O[C@H](Br)[C@H](OC(=O)C(C)(C)C)[C@H]1OC(=O)C(C)(C)C)C(=O)C(C)(C)C

2,3,4,6-O-四特戊酰基-alpha-D-溴代吡喃葡萄糖(81058-27-7)物化性质

实验特性

  • LogP : 4.56920
  • PSA : 114.43000
  • 折射率 : 1.494
  • 沸点 : 530.5°C at 760 mmHg
  • 闪点 : 274.6°C
  • 密度 : 1.22

计算特性

  • 精确分子量 : 578.20900
  • 氢键供体数量 : 0
  • 氢键受体数量 : 9
  • 可旋转化学键数量 : 13
  • 同位素质量 : 578.20905g/mol
  • 重原子数量 : 36
  • 复杂度 : 824
  • 同位素原子数量 : 0
  • 确定原子立构中心数量 : 5
  • 不确定原子立构中心数量 : 0
  • 确定化学键立构中心数量 : 0
  • 不确定化学键立构中心数量 : 0
  • 共价键单元数量 : 1
  • 疏水参数计算参考值(XlogP) : 7.1
  • 拓扑分子极性表面积 : 114Ų

2,3,4,6-O-四特戊酰基-alpha-D-溴代吡喃葡萄糖(81058-27-7)安全信息

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2,3,4,6-O-四特戊酰基-alpha-D-溴代吡喃葡萄糖(81058-27-7)合成路线

合成路线:1 步
反应条件:
参考文献:
High-yield syntheses of tetra-O-benzyl-α-D-glucopyranosyl bromide and tetra-O-pivaloyl-α-D-glucopyranosyl bromide and their advantage in the Koenigs-Knorr reaction
Presser, Armin; et al, Monatshefte fuer Chemie, 2006, 137(3), 365-374
合成路线:1 步
反应条件:
参考文献:
Stereoselective C-Glycosylation Reactions with Arylzinc Reagents
Lemaire, Sebastien; et al, Organic Letters, 2012, 14(6), 1480-1483
合成路线:1 步
反应条件:
参考文献:
Glycosyl-Radical-Based Synthesis of C-Alkyl Glycosides via Photo-mediated Defluorinative gem-Difluoro-allylation
Li, Cai-Yi; et al, Organic Letters, 2021, 23(22), 8899-8904
合成路线:1 步
反应条件:
参考文献:
Excited-State Palladium-Catalyzed 1,2-Spin-Center Shift Enables Selective C-2 Reduction, Deuteration, and Iodination of Carbohydrates
Zhao, Gaoyuan; et al, Journal of the American Chemical Society, 2021, 143(4), 1728-1734
合成路线:1 步
反应条件:
参考文献:
Total Syntheses of Rhodiolosides A and D and of Sachalinols A-C
Simon, Kristina; et al, European Journal of Organic Chemistry, 2011, (8), 1493-1503
合成路线:2 步
反应条件:
参考文献:
Stereoselective C-Glycosylation Reactions with Arylzinc Reagents
Lemaire, Sebastien; et al, Organic Letters, 2012, 14(6), 1480-1483

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