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【结 构 式】 
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【分子编号】16003 【品名】N-methylurea; methyl-urea 【CA登记号】598-50-5 |
【 分 子 式 】C2H6N2O 【 分 子 量 】74.08252 【元素组成】C 32.43% H 8.16% N 37.81% O 21.6% |
合成路线1
该中间体在本合成路线中的序号：(II)By cyclization of glyoxylic acid butyl ester (I) with N-methylurea in refluxing acetic acid/water.
| 【1】 Ienaga, K.; Nakamura, K. (Nippon Zoki Pharmaceutical Co., Ltd.); Hydantoin derivs. and pharmaceutical compsns. containing them. AU 8539172; EP 0160618; ES 8609272; JP 1986122275; US 4647574 . |
合成路线2
该中间体在本合成路线中的序号：(II)The synthesis of aranoza (IV) was accomplished by the condensation of N-methylurea (II) with L-arabinose (I), which yields 3-a-L-arabinopyranosyl-1-methylurea (III), followed by nitrosation of the latter. In slightly alkaline conditions or upon heating, aranoza undergoes intramolecular carbamoylation to produce N1O3-carbonyl-a-L-arabinopyranosylamine (V), gaseous N2 and methanol. It is important that diazomethane (CH2N2) is not formed under these conditions as demonstrated by gas chromatography and mass spectrometry.
| 【1】 Perevodchikova, N.I.; Gorbacheva, L.B.; Preobrazhenskaya, M.N.; Aranoza. Drugs Fut 2003, 28, 10, 941. |
| 【2】 Preobrazhenskaja, M.N.; Miniker, T.D.; Yartseva, I.V.; Kikot, B.S.; Nikitina, T.V.; Ignat'eva, E.V.; Pichugina, L.V.; Timofeeva, A.K.; Kenke, I.K.; Murkhanov, V.I.; Method of synthesis of 3-(1-alpha-L-arabinopyranozyl)-1-methyl-1-nitrosourea (aranose) - an antitumor preparation. SU 1711456 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 16002 | alpha-L-arabinopyranose; Tetrahydro-2H-pyran-2,3,4,5-tetrol; L(+)-Arabinosa | 7296-56-2 | C5H10O5 | 详情 | 详情 |
| (II) | 16003 | N-methylurea; methyl-urea | 598-50-5 | C2H6N2O | 详情 | 详情 |
| (III) | 16004 | N-methyl-N'-[(2R,3R,4S,5S)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl]urea; N-methyl-N'-(3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)urea | C7H14N2O5 | 详情 | 详情 | |
| (V) | 16005 | (1S,5R,8S,9R)-8,9-dihydroxy-2,6-dioxa-4-azabicyclo[3.3.1]nonan-3-one; 1-methyl-2-oxo-N-(3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)-1-hydrazinecarboxamide | C6H9NO5 | 详情 | 详情 |