(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 -Drug Synthesis Database

【结构式】

【分子编号】16005

【品名】(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

【CA登记号】

【分子式】C₆H₉NO₅

【分子量】175.1412

【元素组成】C 41.15% H 5.18% N 8% O 45.68%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(V)

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.

参考文献中间体

合成目标

【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

Extended Information