Sodium valerate; Sodium pentanoate -Drug Synthesis Database

【结构式】

【分子编号】31907

【品名】Sodium valerate; Sodium pentanoate

【CA登记号】

【分子式】C₅H₉NaO₂

【分子量】124.115028

【元素组成】C 48.39% H 7.31% Na 18.52% O 25.78%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(A)

The reaction of daunomycin (I) with trifluoroacetic anhydride in chloroform, and boiling the reaction product with methanol gives N-trifluoroacetyldaunomycin (II), which upon treatment with iodine and calcium oxide in THF gives 14-iodo-N-trifluoroacetyldaunomycin (III). Compound (III) treated with sodium valerate (A) in boiling acetone gives the title compound. The final purification is achieved with silicic acid using chloroform-ethanol (100:1) as solvent.

参考文献中间体

合成目标

【1】 Israel, M.; et al.; N-Trifluoroacetyladriamycin-14-valerate, an analog with greater experimental antitumor avtivity and less toxicity than adriamycin. Cancer Res 1975, 35, 1365-68.
【2】 Israel, M.; Modest, E.J. (Sidney Farber Cancer Institute, Inc.); N-trifluoroacetyladriamycin-14-alkanoates and therapeutic compositions containing same. CA 1060003; US 4035566 .
【3】 Albonico, S.M.; AD-32. Drugs Fut 1980, 5, 4, 171.

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)	31907	Sodium valerate; Sodium pentanoate		C₅H₉NaO₂	详情	详情
(I)	18698	7-(3-Amino-2,3,6-trideoxy-L-lyxo-hexosyloxy)-9-acetyl-7,8,9,10-tetrahydro-6,9,11-trihydroxy-4-methoxy-5,12-naphthacenequinone; (8S,10S)-8-acetyl-10-[[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-5,12-naphthacenedione; (1S,3S)-3-Acetyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1-naphthacenyl 3-amino-2,3,6-trideoxy-alpha-lyxo-hexopyranoside; Daunomycin	20830-81-3	C₂₇H₂₉NO₁₀	详情	详情
(II)	28760	N-Trifluoroacetyldaunomycin; N-((2S,3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy]-3-hydroxy-2-methyltetrahydro-2H-pyran-4-yl)-2,2,2-trifluoroacetamide		C₂₉H₂₈F₃NO₁₁	详情	详情
(III)	32677	14-Iodo-N-trifluoroacetyldaunomycin; 2,2,2-trifluoro-N-((2S,3S,4S,6R)-3-hydroxy-2-methyl-6-[[(1S,3S)-3,5,12-trihydroxy-3-(2-iodoacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy]tetrahydro-2H-pyran-4-yl)acetamide		C₂₉H₂₇F₃INO₁₁	详情	详情

合成路线2

该中间体在本合成路线中的序号：(A)

This compound can be obtained in two different ways: 1) By reaction of phthalic anhydride (I) with valeric anhydride (II) in the presence of sodium valerate (A). 2) By reaction of 2-iodobenzoic acid (III) with copper propylacetylide (IV).

参考文献中间体

合成目标

【1】 Castro, C.E.; et al.; Indoles, benzofurans, phthalides and tolanes via copper (I) acetylides. J Org Chem 1966, 31, 12, 4071-78.
【2】 Lardelli, G.; et al.; A new gamma-lactone found in butter. Recl Trav Chim Pays-Bas 1966, 85, 43-55.
【3】 Castaner, J.; Blancafort, P.; Hillier, K.; Serradell, M.N.; Butylidenephthalide. Drugs Fut 1981, 6, 4, 216.

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)	31907	Sodium valerate; Sodium pentanoate		C₅H₉NaO₂	详情	详情
(I)	11900	2-Benzofuran-1,3-dione;1,2-Benzenedicarboxylic Anhydride;1,2-BENZENE DICARBOXYLIC ACID ANHYDRIDE;1,2-BENZENEDICARBONIC ACID, ANHYDRIDE;1,3-DIOXOPHTHALAN;1,3-ISOBENZOFURANDIONE;o-phthalic anhydride; Phthalic anhydride	85-44-9	C₈H₄O₃	详情	详情
(II)	27683	pentanoic anhydride	2082-59-9	C₁₀H₁₈O₃	详情	详情
(III)	37160	2-iodobenzoic acid	88-67-5	C₇H₅IO₂	详情	详情
(IV)	29069	1-pentynylcopper		C₅H₇Cu	详情	详情

合成路线3

该中间体在本合成路线中的序号：(III)

Ftalic anhydride (I) id treated with butyric anhydride (II) and sodium butyrate to obtain lactone (IV), which is hydrogenated to target compound by means H2 Nickel Raney.

参考文献中间体

合成目标

【1】 Fang, H.J.; Chen, Y.W.; Sun, S.W.; Hu, Q.; Yang, J.S.; Studies on chemical constituents of volatile oil from Apium graveolens seeds. Chin Drug Analyt J 1984, 4, 205.
【2】 Chen, Y.W.; Yang, J.S.; Isolation and determination of active components of Apium graveolens. Chin Pharm Bull 1984, 19, 670.
【3】 Wang, X.-W.; 3-n-Butylphthalide. Drugs Fut 2000, 25, 1, 16.

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)	11900	2-Benzofuran-1,3-dione;1,2-Benzenedicarboxylic Anhydride;1,2-BENZENE DICARBOXYLIC ACID ANHYDRIDE;1,2-BENZENEDICARBONIC ACID, ANHYDRIDE;1,3-DIOXOPHTHALAN;1,3-ISOBENZOFURANDIONE;o-phthalic anhydride; Phthalic anhydride	85-44-9	C₈H₄O₃	详情	详情
(II)	27683	pentanoic anhydride	2082-59-9	C₁₀H₁₈O₃	详情	详情
(III)	31907	Sodium valerate; Sodium pentanoate		C₅H₉NaO₂	详情	详情
(IV)	31908	3-[(Z)butylidene]-2-benzofuran-1-one	551-08-6	C₁₂H₁₂O₂	详情	详情

Extended Information