N,N-bis(trimethylsilyl)amine; trimethyl-N-(trimethylsilyl)silanamine -Drug Synthesis Database

【结构式】

【分子编号】34273

【品名】N,N-bis(trimethylsilyl)amine; trimethyl-N-(trimethylsilyl)silanamine

【CA登记号】999-97-3

【分子式】C₆H₁₉NSi₂

【分子量】161.3946

【元素组成】C 44.65% H 11.87% N 8.68% Si 34.8%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(A)

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

合成路线2

该中间体在本合成路线中的序号：

Coupling of 4-bromo-1-butene (I) with catecholborane (II) afforded the bromobutyl boronate (III). Subsequent exchange of (III) with alpha-pinanediol (IV) produced (V), which was regioselectively chlorinated to give (VI). Displacement of the chlorine atom of (VI) with lithium hexamethyldisilazide, followed by acid treatment furnished intermediate (VII).

参考文献中间体

合成目标

【1】 Verbeuren, T.; Rupin, A.; De Nanteuil, G.; Gloanec, P.; New dicarbonyl cycloalkyl based thrombin inhibitors with improved activity and selectivity compared to (D)-Phe-Pro-boroArg derivatives . 218th ACS Natl Meet (Aug 22 1999, New Orleans) 1999, Abst MEDI 201.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	34273	N,N-bis(trimethylsilyl)amine; trimethyl-N-(trimethylsilyl)silanamine	999-97-3	C₆H₁₉NSi₂	详情	详情
(I)	11720	4-Bromo-1-butene	5162-44-7	C₄H₇Br	详情	详情
(II)	32533	1,3,2-benzodioxaborole	274-07-7	C₆H₅BO₂	详情	详情
(III)	32534	2-(4-bromobutyl)-1,3,2-benzodioxaborole		C₁₀H₁₂BBrO₂	详情	详情
(IV)	32535	(1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol		C₁₀H₁₈O₂	详情	详情
(V)	32536	(1R,2S,6R,8R)-4-(5-bromopentyl)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]decane		C₁₅H₂₆BBrO₂	详情	详情
(VI)	32537	(1R,2S,6R,8R)-4-[(1R)-5-bromo-1-chloropentyl]-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]decane		C₁₅H₂₅BBrClO₂	详情	详情
(VII)	32538	(1R)-5-bromo-1-[(1R,2S,6R,8R)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]-1-pentanamine; (1R)-5-bromo-1-[(1R,2S,6R,8R)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]pentylamine		C₁₅H₂₇BBrNO₂	详情	详情

Extended Information