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【结 构 式】

【分子编号】20179

【品名】ethyl (E)-4-pentadecenoate

【CA登记号】

【 分 子 式 】C17H32O2

【 分 子 量 】268.43988

【元素组成】C 76.06% H 12.02% O 11.92%

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)

1) The reaction of undecanal (I) with vinylmagnesium bromide (II) in THF gives 1-tridecen-3-ol (III), which is condensed with propionic acid (IV) by means of triethyl orthoacetate in refluxing xylene yielding 4(E)-pentadecenoic acid ethyl ester (V). The reaction of (V) with AD-mix-beta and methanesulfonamide in tert-butanol affords (R,R)-5-(1-hydroxyundecyl)tetrahydrofuran-2-one (VI), which by reaction with p-nitrobenzoic acid and triphenylphosphine in benzene gives the corresponding ester (VII). The reaction of (VII) first with LiAlH4 in ether, followed by a treatment with acetone and p-toluenesulfonic acid yields the acetonide (VIII), which by oxidation of its primary alcohol with pyridinium chlorochromate (PCC) in dichloromethane affords the corresponding aldehyde (IX). The reaction of (IX) with vinylmagnesium bromide (II) in ether gives the allyl alcohol (X), which by condensation with proionic acid (IV) and triethyl orthoacetate yields (4E,8R,9S)-8,9-(isopropylidenedioxy)-4-nonadecenoic acid ethyl ester (XI), The reduction of (XI) with diisobutylaluminum hydride (DIBAL) in toluene affords the corresponding aldehyde (XII), which is condensed with triethyl phosphonoacetate (XIII) by means of NaH in toluene giving (2E,6E,10R,11S)-10,11-(isopropylidenedioxy)-heneicosa-2,6-dienoic acid ethyl ester (XIV).

1 Yazbak, A.; et al.; Total synthesis of uvaricin. J Org Chem 1998, 63, 17, 5863.
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) 20175 undecanal 112-44-7 C11H22O 详情 详情
(II) 10386 Allyl(bromo)magnesium 1730-25-2 C3H5BrMg 详情 详情
(III) 20177 1-tridecen-3-ol C13H26O 详情 详情
(IV) 20178 propionic acid 79-09-4 C3H6O2 详情 详情
(V) 20179 ethyl (E)-4-pentadecenoate C17H32O2 详情 详情
(VI) 20180 (5R)-5-[(1R)-1-hydroxyundecyl]dihydro-2(3H)-furanone C15H28O3 详情 详情
(VII) 20181 (1R)-1-[(2S)-4-oxo-1,3-dioxolan-2-yl]undecyl 4-nitrobenzoate C21H29NO7 详情 详情
(VIII) 20182 3-[(4R,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl]-1-propanol C18H36O3 详情 详情
(IX) 20183 3-[(4R,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl]propanal C18H34O3 详情 详情
(X) 20184 (3S)-5-[(4R,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl]-1-penten-3-ol C20H38O3 详情 详情
(XI) 20185 ethyl (E)-7-[(4R,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl]-4-heptenoate C24H44O4 详情 详情
(XII) 20186 (E)-7-[(4R,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl]-4-heptenal C22H40O3 详情 详情
(XIII) 10019 Ethyl 2-(diethoxyphosphoryl)acetate; Triethyl phosphonoacetate 867-13-0 C8H17O5P 详情 详情
(XIV) 20188 ethyl (2E,6E)-9-[(4R,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2,6-nonadienoate C26H46O4 详情 详情
Extended Information