9-{[(E)-1-(phenylsulfanyl)-1-propenyl]oxy}-9-borabicyclo[3.3.1]nonane; (E)-1-(9-borabicyclo[3.3.1]non-9-yloxy)-1-propenyl phenyl sulfide -Drug Synthesis Database

【结构式】

【分子编号】54620

【品名】9-{[(E)-1-(phenylsulfanyl)-1-propenyl]oxy}-9-borabicyclo[3.3.1]nonane; (E)-1-(9-borabicyclo[3.3.1]non-9-yloxy)-1-propenyl phenyl sulfide

【CA登记号】

【分子式】C₁₇H₂₃BOS

【分子量】286.24602

【元素组成】C 71.33% H 8.1% B 3.78% O 5.59% S 11.2%

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)

The reaction of N-Boc-L-prolinal (VII) with the boron enolate (VIII) in ethyl ether gives the chiral beta-hydroxythioester (IX), which is transesterified with K2CO3 and ethanol to afford the beta-hydroxypropionate (X). The methylation of the OH group of (X) with LiHMDS and Me-OTf as before provides the methoxyester (XI), which is finally hydrolyzed with LiOH in aq. ethanol to furnish the desired intermediate, the methoxy amino acid (XII).

参考文献中间体

合成目标

【1】 Tomioka, K.; et al.; An expeditious synthesis of dolastatin 10. Tetrahedron 1991, 32, 21, 2395.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(VII)	16734	(2S)-1-(tert-butoxycarbonyl)tetrahydro-1H-pyrrole-2-carboxylic acid; N-alpha-t-BOC-L-proline; (2S)-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid	C₁₀H₁₇NO₄	详情	详情
(VIII)	54620	9-{[(E)-1-(phenylsulfanyl)-1-propenyl]oxy}-9-borabicyclo[3.3.1]nonane; (E)-1-(9-borabicyclo[3.3.1]non-9-yloxy)-1-propenyl phenyl sulfide	C₁₇H₂₃BOS	详情	详情
(IX)	54621	tert-butyl (2S)-2-[(1R,2R)-1-hydroxy-2-methyl-3-oxo-3-(phenylsulfanyl)propyl]-1-pyrrolidinecarboxylate	C₁₉H₂₇NO₄S	详情	详情
(X)	54622	tert-butyl (2S)-2-[(1R,2R)-3-ethoxy-1-hydroxy-2-methyl-3-oxopropyl]-1-pyrrolidinecarboxylate	C₁₅H₂₇NO₅	详情	详情
(XI)	54623	tert-butyl (2S)-2-[(1R,2R)-3-ethoxy-1-methoxy-2-methyl-3-oxopropyl]-1-pyrrolidinecarboxylate	C₁₆H₂₉NO₅	详情	详情
(XII)	23520	(2R,3R)-3-[(2S)-1-(tert-butoxycarbonyl)pyrrolidinyl]-3-methoxy-2-methylpropionic acid	C₁₄H₂₅NO₅	详情	详情

Extended Information