benzyl (2R,3S,4R)-4-(benzyloxy)-2-[(benzyloxy)methyl]-5-bromotetrahydro-3-furanyl ether; (2R,3S,4R)-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5-bromotetrahydrofuran -Drug Synthesis Database

【结构式】

【分子编号】34271

【品名】benzyl (2R,3S,4R)-4-(benzyloxy)-2-[(benzyloxy)methyl]-5-bromotetrahydro-3-furanyl ether; (2R,3S,4R)-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5-bromotetrahydrofuran

【CA登记号】

【分子式】C₂₆H₂₇BrO₄

【分子量】483.40198

【元素组成】C 64.6% H 5.63% Br 16.53% O 13.24%

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：(III)

Treatment of 2,4-dihydroxypyridine (I) with hexamethyldisilazane (A) gives 2,4-bis(trimethylsilyloxy)pyridine (II). Condensation of (II) with 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide (III) gives a 68% yield 2',3',5'-tri-O-benzoyl-3-deazauridine (IV). Deblocking of (IV) with alcoholic ammonia gives 3-deazauridine in 88% crude yield.

参考文献中间体

合成目标

【1】 Currie, B.L.; et al.; Synthesis of 3-deazauridine-[4-hydoxy-1-(beta-D-ribofuranosyl)-2-pyridone]. Chem Commun 1968, 1547-48.
【2】 Currie, B.L.; et al.; The synthesis of 3-deazapyrimidine nucleosides related to uridine and cytidine and their derivatives. J Heterocycl Chem 1970, 7, 323-329.
【3】 Chang, P.; 3-Deazauridine. Drugs Fut 1984, 9, 10, 739.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	34273	N,N-bis(trimethylsilyl)amine; trimethyl-N-(trimethylsilyl)silanamine	999-97-3	C₆H₁₉NSi₂	详情	详情
(I)	34269	2,4-pyridinediol	626-03-9	C₅H₅NO₂	详情	详情
(II)	34270	trimethylsilyl 2-[(trimethylsilyl)oxy]-4-pyridinyl ether; 2,4-bis[(trimethylsilyl)oxy]pyridine		C₁₁H₂₁NO₂Si₂	详情	详情
(III)	34271	benzyl (2R,3S,4R)-4-(benzyloxy)-2-[(benzyloxy)methyl]-5-bromotetrahydro-3-furanyl ether; (2R,3S,4R)-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5-bromotetrahydrofuran		C₂₆H₂₇BrO₄	详情	详情
(IV)	34272	1-[(2R,3R,4S,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]tetrahydro-2-furanyl]-4-hydroxy-2(1H)-pyridinone		C₃₁H₃₁NO₆	详情	详情

Extended Information