tert-butyl (1S)-1-(sec-butyl)-2-oxo-4-pentenylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】54596

【品名】tert-butyl (1S)-1-(sec-butyl)-2-oxo-4-pentenylcarbamate

【CA登记号】

【分子式】C₁₄H₂₅NO₃

【分子量】255.35744

【元素组成】C 65.85% H 9.87% N 5.49% O 18.8%

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 reaction of N-Boc-L-isoleucine (I) with O-methylhydroxylamine (II) by means of PyBOP gives the corresponding amide (III), which is condensed with allylmagnesium bromide (IV) to afford the octenone (V). The reduction of (V) with NaBH4 yields the carbinol (VI), which is N- and O-methylated with Me-I and NaH to provide the dimethylated compound (VII). Finally, the terminal double bond of (VII) is oxidated by means of NaIO4 and RuO2 to furnish the desired intermediate, the amino acid (VIII).

参考文献中间体

合成目标

【1】 Roux, F.; et al.; Synthesis of dolastatin-10 and [R-Doe]-dolastatin-10. Tetrahedron 1994, 50, 18, 5345.

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)	30009	(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-methylpentanoic acid	13139-16-7	C₁₁H₂₁NO₄	详情	详情
(II)	13361	(Methoxyamino)methane; N,O-Dimethylhydroxylamine	1117-97-1	C₂H₇NO	详情	详情
(III)	38788	tert-butyl (1S,2S)-1-[[methoxy(methyl)amino]carbonyl]-2-methylbutylcarbamate	3350-19-4	C₁₃H₂₆N₂O₄	详情	详情
(IV)	10386	Allyl(bromo)magnesium	1730-25-2	C₃H₅BrMg	详情	详情
(V)	54596	tert-butyl (1S)-1-(sec-butyl)-2-oxo-4-pentenylcarbamate		C₁₄H₂₅NO₃	详情	详情
(VI)	54597	tert-butyl (1S,2R)-1-(sec-butyl)-2-hydroxy-4-pentenylcarbamate		C₁₄H₂₇NO₃	详情	详情
(VII)	54598	tert-butyl (1S,2R)-1-(sec-butyl)-2-methoxy-4-pentenyl(methyl)carbamate		C₁₆H₃₁NO₃	详情	详情
(VIII)	54599	(3R,4S)-4-[(tert-butoxycarbonyl)(methyl)amino]-3-methoxy-5-methylheptanoic acid		C₁₅H₂₉NO₅	详情	详情

Extended Information