bromo(2-naphthyl)magnesium -Drug Synthesis Database

【结构式】

【分子编号】33688

【品名】bromo(2-naphthyl)magnesium

【CA登记号】

【分子式】C₁₀H₇BrMg

【分子量】231.37458

【元素组成】C 51.91% H 3.05% Br 34.53% Mg 10.5%

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：(VIII)

Addition of 2-naphthylmagnesium bromide (VIII) produced the corresponding carbinol as a diastereomeric mixture, from which the required isomer (IX) was isolated by preparative TLC. Finally, the silyl protecting group was cleaved by treatment with HF in pyridine.

参考文献中间体

合成目标

【1】 Sinclair, P.J.; Organ, H.M.; Wong, F.; Goulet, M.; Parsons, W.H.; Wyvratt, Matthew, J.; O-Aryl, O-alkyl, O-alkenyl and O-alkynylmacrolides having immunosuppressive activity. US 5565560 .
【2】 Sinclair, P.J.; Goulet, J.; Wong, F.; Goulet, M.; Parsons, W.H.; Wyvratt, Matthew, J.; O-Heteroaryl, O-alkylheteroaryl, O-alkenylheteroaryl and O-alkynylheteroarylmacrolides having immunosuppressive activity. US 5349061 .
【3】 Wong, F.; Holmes, M.A.; Armstrong, H.M.; et al.; Potent immunosuppressive C32-O-arylethyl ether derivatives of ascomycin with reduced toxicity. Bioorg Med Chem Lett 1999, 9, 14, 2089-94.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(VII)	22758	2-([(1R,2R,4R)-4-[(E)-2-((1R,9S,12S,13S,14S,17R,21S,23S,24R,25S,27R)-14-[[tert-butyl(dimethyl)silyl]oxy]-17-ethyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-2,3,10,16-tetraoxo-11,28-dioxa-4-azatricyclo[22.3.1.0(4,9)]octacos-18-en-12-yl)-1-propenyl]-2-methoxycyclohexyl]oxy)acetaldehyde	C₅₁H₈₅NO₁₃Si	详情	详情
(VIII)	33688	bromo(2-naphthyl)magnesium	C₁₀H₇BrMg	详情	详情
(IX)	33689	(1R,9S,12S,13S,14S,17R,21S,23S,24R,25S,27R)-14-[[tert-butyl(dimethyl)silyl]oxy]-17-ethyl-1-hydroxy-12-[(E)-2-((1R,3R,4R)-4-[[(2S)-2-hydroxy-2-(2-naphthyl)ethyl]oxy]-3-methoxycyclohexyl)-1-methylethenyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0(4,9)]octacos-18-ene-2,3,10,16-tetrone	C₆₁H₉₃NO₁₃Si	详情	详情

Extended Information