2′-O-(2-Methoxyethyl)-5-methyluridine CAS#: 163759-49-7; 凯望编码 (ChemWhat Code): 427548
Identification
| 英文名 | 2′-O-(2-Methoxyethyl)-5-methyluridine |
| IUPAC Name | 1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-(2-methoxyethoxy)oxolan-2-yl]-5-methylpyrimidine-2,4-dione |
| 分子结构 |  |
| CAS编号 | 163759-49-7 |
| MDL Number | MFCD02682964 |
| 别名 | 163759-49-7 2′-O-(2-Methoxyethyl)-5-methyl-uridine 2′-O-(2-methoxyethyl)-5-methylUridine Uridine, 2′-O-(2-methoxyethyl)-5-methyl- 2′-O-MOE-5-Me-rU 9Q36I4D9VB 1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-(2-methoxyethoxy)oxolan-2-yl]-5-methylpyrimidine-2,4-dione 1-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-(2-methoxyethoxy)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 2′-MOE-5-Methyluridine UNII-9Q36I4D9VB SCHEMBL50826 DTXSID10459964 2’O-Methoxyethyl-5-methyluridine NEVQCHBUJFYGQO-DNRKLUKYSA-N 2′-o-methoxyethyl-5-methyluridine 2′-O-Methoxvethyl-5-methyluridine 2′–O-Methoxyethyl-5-methyluridine MFCD02682964 2′-O-(methoxyethyl)-5-methyluridine 2′–O–Methoxyethyl-5-methyluridine AKOS016005091 AM10114 HY-W048488 AC-24669 BP-58846 CS-16579 CS-0100774 F12191 A851922 J-700309 1-((2R,3R,4R,5R)-3-(2-methoxyethoxy)-tetrahydro-4-hydroxy-5-(hydroxymethyl)furan-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione |
| 分子式 | C13H20N2O7 |
| 分子量 | 316.31 |
| InChI | InChI=1S/C13H20N2O7/c1-7-5-15(13(19)14-11(7)18)12-10(21-4-3-20-2)9(17)8(6-16)22-12/h5,8-10,12,16-17H,3-4,6H2,1-2H3,(H,14,18,19)/t8-,9-,10-,12-/m1/s1 |
| InChI Key | NEVQCHBUJFYGQO-DNRKLUKYSA-N |
| Isomeric SMILES | CC1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)OCCOC |
Physical Data
| Appearance | White powder |
| Melting Point, °C | Solvent (Melting Point) |
| 115.5 – 116.5 | ethyl acetate |
| 115.5 – 116.5 | |
| 115.5 – 116.5 | methanol, ethyl acetate |
Spectra
Route of Synthesis (ROS)
| Conditions | Yield |
| Stage #1: O-2,2′-cyclo-5-methyluridine; tris(2-methoxyethyl)borate With sodium hydrogencarbonate In 2-methoxy-ethanol at 130℃; for 21h; Stage #2: With water for 0.5h; Heating / reflux; Experimental Procedure 2,2′-Anhydro-5-methyl-uridine (2000 g, 8.32 mol), tris(2-methoxyethyl)borate (2504 g, 10.60 mol), sodium bicarbonate (60 g, 0.70 mol) and anhydrous 2-methoxyethanol (5 L) were combined in a 12 L three necked flask and heated to 130° C. (internal temp) at atmospheric pressure, under an argon atmosphere with stirring for 21 h. TLC indicated a complete reaction. The solvent was removed under reduced pressure until a sticky gum formed (50-85° C. bath temp and 100-11 mm Hg) and the residue was redissolved in water (3 L) and heated to boiling for 30 min in order the hydrolyze the borate esters. The water was removed under reduced pressure until a foam began to form and then the process was repeated. HPLC indicated about 77% product, 15% dimer (5′ of product attached to 2′ of starting material) and unknown derivatives, and the balance was a single unresolved early eluting peak. [0176] The gum was redissolved in brine (3 L), and the flask was rinsed with additional brine (3 L). The combined aqueous solutions were extracted with chloroform (20 L) in a heavier-than continuous extractor for 70 h. The chloroform layer was concentrated by rotary evaporation in a 20 L flask to a sticky foam (2400 g). This was coevaporated with MeOH (400 mL) and EtOAc (8 L) at 75° C. and 0.65 atm until the foam dissolved at which point the vacuum was lowered to about 0.5 atm. After 2.5 L of distillate was collected a precipitate began to form and the flask was removed from the rotary evaporator and stirred until the suspension reached ambient temperature. | 69.4% |
Safety and Hazards
No data available
Other Data
| Transportation | Storage at -20°，keep away from light and sealed |
| HS Code | |
| Storage | Storage at -20°，keep away from light and sealed |
| Shelf Life | 1 year |
| Market Price |
| Druglikeness | |
| Lipinski rules component | |
| 分子量 | 316.311 |
| logP | -2.036 |
| HBA | 9 |
| HBD | 3 |
| Matching Lipinski Rules | 4 |
| Veber rules component | |
| Polar Surface Area (PSA) | 117.56 |
| Rotatable Bond (RotB) | 6 |
| Matching Veber Rules | 2 |
| Use Pattern |
| 3-Aminopyridine CAS#: 462-08-8 is an intermediate in pesticides and dyes; pesticide raw materials; analytical reagents. |
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