(3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl 4-aminobutanoate -Drug Synthesis Database

【结构式】

【分子编号】59013

【品名】(3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl 4-aminobutanoate

【CA登记号】

【分子式】C₁₀H₁₉NO₇

【分子量】265.2634

【元素组成】C 45.28% H 7.22% N 5.28% O 42.22%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(IV)

Esterification of glucose diacetonide (I) with N-Boc-gamma-aminobutyric acid (II) in the presence of DCC and DMAP provides the protected glucose-3-ester (III). Hydrolysis of (III) with trifluoroacetic acid in CH2Cl2 leads to the 3-GABA-glucose (IV).

参考文献中间体

合成目标

【1】 Jacob, J.N. (Organomed Corporation); Paclitaxel-carbohydrate conjugates: Design, synthesis and biological evaluations. US 6218367 .

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)	59011	(5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol		C₁₂H₂₀O₆	详情	详情
(II)	39226	4-[(tert-butoxycarbonyl)amino]butyric acid;4-((tert-butoxycarbonyl)amino)butanoic acid	57294-38-9	C₉H₁₇NO₄	详情	详情
(III)	59012	(5S,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl 4-[(tert-butoxycarbonyl)amino]butanoate		C₂₁H₃₅NO₉	详情	详情
(IV)	59013	(3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl 4-aminobutanoate		C₁₀H₁₉NO₇	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

Condensation of paclitaxel (V) with succinic anhydride (VI) affords the hemisuccinate ester (VII). This is subsequently coupled with amino ester (IV) in the presence of DCC to furnish the title compound.

参考文献中间体

合成目标

【1】 Jacob, J.N. (Organomed Corporation); Paclitaxel-carbohydrate conjugates: Design, synthesis and biological evaluations. US 6218367 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	59013	(3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl 4-aminobutanoate		C₁₀H₁₉NO₇	详情	详情
(V)	10595	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy]-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate	33069-62-4	C₄₇H₅₁NO₁₄	详情	详情
(VI)	11291	Dihydro-2,5-furandione; Succinic anhydride	108-30-5	C₄H₄O₃	详情	详情
(VII)	59014	4-{[(1R,2S)-2-(benzoylamino)-1-({[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-2-(benzoyloxy)-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-15-yl]oxy}carbonyl)-2-phenylethyl]oxy}-4-oxobutano		C₅₁H₅₅NO₁₇	详情	详情

Extended Information