2-脱氧-2-氟-三苯甲酰基-α-D-阿垃伯呋喃糖 | 97614-43-2
中文名称:
2-脱氧-2-氟-三苯甲酰基-α-D-阿垃伯呋喃糖
英文名称:
[(2R,3R,4S,5R)-3,5-bis(benzoyloxy)-4-fluorooxolan-2-yl]methyl benzoate
CAS No.:
97614-43-2
分子式:
C2 6 H2 1 FO7
分子量:
464.439151525497
名称和标识符
MDL
MFCD00083339
InChIKey
JOAHVPNLVYCSAN-UXGLMHHASA-N
Inchi
1S/C26H21FO7/c27-21-22(33-24(29)18-12-6-2-7-13-18)20(16-31-23(28)17-10-4-1-5-11-17)32-26(21)34-25(30)19-14-8-3-9-15-19/h1-15,20-22,26H,16H2/t20-,21+,22-,26-/m1/s1
SMILES
O([C@H]1[C@H](F)[C@@H](OC(C2C=CC=CC=2)=O)O[C@@H]1COC(C1C=CC=CC=1)=O)C(C1C=CC=CC=1)=O
别名信息
- 中文别名 -
2-脱氧-2-氟-三苯甲酰基-α-D-阿垃伯呋喃糖
克罗垃滨中间体
2-脱氧-2-氟-1,3,5-三苯甲酰基-α-D-阿垃伯呋喃糖
氟糖
2-脱氧-2-氟-1,3,5-三苯甲酰基-alpha-D-阿拉伯呋喃糖
2-脱氧-2-氟-1,3,5-三-O-苯甲酰基-α-D-阿拉伯呋喃糖
1,3,5-三-O-苯甲酰基-2-脱氧-2-氟-α-D-呋喃阿拉伯糖
2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-alpha-D-arabinofuranose 2-脱氧-2-氟-1,3,5-三-O-苯甲酰基-α-D-阿拉伯呋喃糖
2-脱氧-2-氟-1,3,5-三苯甲酰基-alpha-D-阿拉伯呋喃糖 (地西他宾)
2-脱氧-2-氟-1,3,5-三苯甲酰基-alpha-D-阿拉伯呋喃糖,2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose
2-脱氧-2-氟-1,3,5-三苯甲酰基-α-D- 阿拉伯呋喃糖
- 英文别名 -
2-fluoro-2-deoxy-1,3,5-tri-O-benzoyl-*A-D-arabino
2-deoxy-2-fluoro-1,3,5-tri-O-benzoyl-α-D-arabinofuranose
FLuorosugar
2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose
2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-alpha-D-arabinofuranose
(2R,3S,4R,5R)-5-((Benzoyloxy)methyl)-3-fluorotetrahydrofuran-2,4-diyl dibenzoate
1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-alpha-D-arabinofuranose
2-Fluoro-2deoxy-1,3,5-O-benzoyl-a-D-arabinofuranose
a-D-Arabinofuranose,2-deoxy-2-fluoro-, 1,3,5-tribenzoate
1,3,5-Tri-O-Benzoyl-2-Deoxy-2-Fluoro -α-D-Arabinose
2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-arabinofuranose
α-D-Arabinofuranose, 2-deoxy-2-fluoro-, tribenzoate (9CI)
D
2-Deoxy-2-fluoro-α-D-arabinofuranose 1,3,5-tribenzoate
2′-Fluoro-2′-deoxy-1,3,5-tri-O-benzoyl-α-D-arabinofuranose
[(2R,3R,4S,5R)-3,5-bis(benzoyloxy)-4-fluorooxolan-2-yl]methyl benzoate
物化性质
实验特性
LogP
3.98900
PSA
88.13000
折射率
1.607
沸点
584.1°C at 760 mmHg
熔点
83.0 to 87.0 deg-C
闪点
295.7 °C
溶解度
Soluble in chloroform or dichloromethane
颜色与性状
白色结晶粉末
比旋光度
+74 ± 2° (C=1 in CH2Cl2)
密度
1.35
计算特性
海关数据
海关编码
2932190090
海关数据
中国海关编码:
2932190090
概述:
2932190090 其他结构上有非稠合呋喃环化合物. 增值税率:17.0% 退税率:9.0% 监管条件:无 最惠国关税:6.5% 普通关税:20.0%
申报要素:
品名, 成分含量, 用途
Summary:
2932190090 other compounds containing an unfused furan ring (whether or not hydrogenated) in the structure VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:20.0%
合成路线
合成路线:1 步
1.1
Reagents:
Deoxo-Fluor
Solvents:
Dichloromethane
;
50 °C
参考文献:
Synthesis of 2',3'-Dideoxy-2'-fluoro-3'-thioarabinothymidine and its 3'-Phosphoramidite Derivative
Elzagheid, Mohamed I.;
Tedeschi, Anna Lisa;
Damha, Masad J. ,
Nucleosides ,
2003 ,
22(5-8) ,
1343-1346
合成路线:1 步
1.1
Reagents:
Triethylamine trihydrofluoride
Solvents:
Ethyl acetate
;
rt; 3 h, 60 °C; 1.5 h, 70 °C
参考文献:
Synthesis of 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose
Zhu, Lihua;
Chen, Qian;
Xu, Yunfeng;
Fan, Juzheng ,
Huaxi Yaoxue Zazhi ,
2005 ,
20(3) ,
207-210
合成路线:1 步
1.1
Reagents:
(Diethylamino)sulfur trifluoride
Solvents:
Dichloromethane
;
15 h, reflux
参考文献:
Reactivity between acetone and single-stranded DNA containing a 5'-capped 2'-fluoro-N7-methyl guanine
Mohan, Utpal;
Burai, Ritwik;
McNaughton, Brian R. ,
Tetrahedron Letters ,
2014 ,
55(22) ,
3358-3360
合成路线:1 步
1.1
Reagents:
Hydrofluoric acid
Catalysts:
Iron(III) acetylacetonate
Solvents:
1,4-Dioxane
参考文献:
Preparation of fluoro-sugars and other fluoro compounds
,
World Intellectual Property Organization ,
,
,
合成路线:1 步
1.1
Reagents:
Pyridine
,
Trifluoromethanesulfonic acid
Solvents:
Acetonitrile
;
0.5 h, rt
1.2
Reagents:
Triethylamine
,
Triethylamine trihydrofluoride
;
18 h, 50 °C
1.3
Solvents:
Water
参考文献:
Direct and convenient conversion of alcohols to fluorides
Yin, Jingjun;
Zarkowsky, Devin S.;
Thomas, David W.;
Zhao, Matthew M.;
Huffman, Mark A. ,
Organic Letters ,
2004 ,
6(9) ,
1465-1468
合成路线:1 步
1.1
Reagents:
(Diethylamino)sulfur trifluoride
Solvents:
Dichloromethane
;
rt; 12 h, rt → 40 °C; 12 h, 40 °C
1.2
Reagents:
Sodium bicarbonate
Solvents:
Dichloromethane
,
Water
参考文献:
Positron emission tomography probe demonstrates a striking concentration of ribose salvage in the liver
Clark, Peter M.;
Flores, Graciela;
Evdokimov, Nikolai M.;
McCracken, Melissa N.;
Chai, Timothy; et al ,
Proceedings of the National Academy of Sciences of the United States of America ,
2014 ,
111(28) ,
合成路线:1 步
1.1
Reagents:
Triethylamine trihydrofluoride
Solvents:
Ethyl acetate
;
60 °C; 60 °C → 70 °C
1.2
Reagents:
Triethylamine
;
10 h, 70 °C; 70 °C → rt
1.3
Reagents:
Sodium bicarbonate
Solvents:
Water
;
neutralized, cooled
参考文献:
Process for preparation of Clofarabine intermediate 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide
,
China ,
,
,
合成路线:1 步
1.1
Reagents:
Triethylamine
,
Triethylamine trihydrofluoride
Solvents:
Acetonitrile
;
36 h, 60 °C
1.2
Reagents:
Water
参考文献:
Preparation of thiouracil nucleoside analogs for treatment of viruses and cancer
,
India ,
,
,
合成路线:1 步
1.1
Reagents:
(Diethylamino)sulfur trifluoride
Solvents:
Dichloromethane
参考文献:
2'-Deoxy-2'-fluoro-β-D-arabinonucleosides and oligonucleotides (2'F-ANA): synthesis and physicochemical studies
Wilds, Christopher J.;
Damha, Masad J. ,
Nucleic Acids Research ,
2000 ,
28(18) ,
3625-3635
合成路线:1 步
1.1
Reagents:
Triethylamine
,
Hydrofluoric acid
Solvents:
Ethyl acetate
,
Water
;
3 h, 80 °C
1.2
Reagents:
Triethylamine
;
3 h, heated
参考文献:
Synthesis of clofarabine
Chen, Lili;
Cen, Junda ,
Zhongguo Yiyao Gongye Zazhi ,
2006 ,
37(8) ,
508-510
合成路线:1 步
1.1
Reagents:
Triethylamine trihydrofluoride
Solvents:
Ethyl acetate
参考文献:
Triethylamine poly(hydrogen fluorides) in the synthesis of a fluorinated nucleoside glycon
Chou, T. S.;
Becke, Lisa M.;
O'Toole, John C.;
Carr, M. Austin;
Parker, Bruce E. ,
Tetrahedron Letters ,
1996 ,
37(1) ,
17-20
合成路线:1 步
1.1
Reagents:
Triethylamine trihydrofluoride
Solvents:
Ethyl acetate
;
3 h, rt → 60 °C; 1.5 h, 70 °C
1.2
Reagents:
Water
;
cooled
参考文献:
Pharmaceutical application of 2'-fluoro-4'-azido-nucleoside analog or its salt
,
China ,
,
,
合成路线:1 步
1.1
Reagents:
Benzyltriethylammonium chloride
,
Potassium fluoride
Solvents:
Chloroform
,
Water
;
4 h, 60 °C
1.2
Reagents:
Ammonia
Solvents:
Water
;
pH 7 - 8, cooled
参考文献:
Improved synthesis of clofarabine
Guo, Shunmin;
Deng, Sishan;
Qi, Yiping;
Lin, Sui ,
Zhongguo Xiandai Yingyong Yaoxue ,
2009 ,
26(2) ,
123-125
合成路线:1 步
1.1
Reagents:
Triethylamine trihydrofluoride
Solvents:
Ethyl acetate
;
rt → 60 °C; 3 h, 60 °C; 1.5 h, 70 °C
1.2
Reagents:
Sodium chloride
Solvents:
Water
;
cooled
参考文献:
Preparation of 2'-fluoro-4'-substituted nucleoside analogs as antiviral agents
,
China ,
,
,
合成路线:1 步
1.1
Reagents:
Hydrofluoric acid
,
Potassium bifluoride
Solvents:
(±)-Propylene glycol
,
Water
;
rt → 160 °C; 130 - 160 °C; 5 h, 130 - 160 °C; cooled
1.2
Reagents:
Water
;
1 h, cooled
参考文献:
Method for preparing clofarabine with high yield
,
China ,
,
,
合成路线:1 步
1.1
Reagents:
Deoxo-Fluor
Solvents:
Toluene
1.2
Reagents:
Sodium bicarbonate
Solvents:
Water
参考文献:
Synthesis of 2-deoxy-2-fluoro-arabinose derivatives
,
European Patent Organization ,
,
,
合成路线:1 步
1.1
Reagents:
(Diethylamino)sulfur trifluoride
Solvents:
Dichloromethane
;
15 h, reflux
参考文献:
Synthesis and Structure of Duplex DNA Containing the Genotoxic Nucleobase Lesion N7-Methylguanine
Lee, Seongmin;
Bowman, Brian R.;
Ueno, Yoshihito;
Wang, Shuyu;
Verdine, Gregory L. ,
Journal of the American Chemical Society ,
2008 ,
130(35) ,
11570-11571
合成路线:1 步
1.1
Reagents:
Deoxo-Fluor
Solvents:
Dichloromethane
;
50 °C
参考文献:
Sulfur, Trifluoro[2-methoxy-N-(2-methoxyethyl)ethanaminato-κN]-,(T-4)-
Cannon, Kevin C.;
Krow, Grant R. ,
e-EROS Encyclopedia of Reagents for Organic Synthesis ,
2010 ,
,
1-7
合成路线:1 步
1.1
Reagents:
(Diethylamino)sulfur trifluoride
Solvents:
Dichloromethane
;
18 h, 40 - 42 °C
参考文献:
Method for synthesizing nucleoside analog clofarabine
,
China ,
,
,
合成路线:1 步
1.1
Reagents:
(T-4)-(4-Carboxyphenyl)trifluorosulfur
Solvents:
Dichloromethane
;
cooled; rt
1.2
Reagents:
Water
;
cooled
参考文献:
Method for preparing 2-deoxy-2-fluoro-α-D-arabinofuranose derivatives
,
China ,
,
,