(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 -Drug Synthesis Database

【结构式】

【分子编号】59012

【品名】(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

【CA登记号】

【分子式】C₂₁H₃₅NO₉

【分子量】445.51024

【元素组成】C 56.62% H 7.92% N 3.14% O 32.32%

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：(III)

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

Extended Information