2,2-dimethyl-5-{3-[(triphenylmethyl)sulfanyl]propyl}-1,3-dioxane-4,6-dione -Drug Synthesis Database

【结构式】

【分子编号】63156

【品名】2,2-dimethyl-5-{3-[(triphenylmethyl)sulfanyl]propyl}-1,3-dioxane-4,6-dione

【CA登记号】

【分子式】C₂₈H₂₈O₄S

【分子量】460.59392

【元素组成】C 73.02% H 6.13% O 13.89% S 6.96%

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：(IV)

Acylation of Meldrum's acid (I) with 3-tryphenylmethylsulfanyl)propionic acid (II) by means of DCC produces the intermediate adduct (III), which is subsequently reduced to the tritylsulfanyl derivative (IV) by using NaBH4/AcOH. Alkylation of (IV) with methyl 3-bromopropionate (V) in the presence of NaOMe provides the 5,5-disubstituted dioxanedione (VI). Basic hydrolysis of (VI) gives rise to the tricarboxylic acid (VII), which is further decarboxylated to (VIII) in hot DMSO. Finally the S-trityl protecting gropu is removed by treatment with trifluoroacetic acid and triisopropylsilane.

参考文献中间体

合成目标

【1】 Jackson, P.F.; Slusher, B.S.; Majer, P.; Maclin, K.M.; Wang, E.; Lapidus, R.S. (Guilford Pharmaceuticals Inc.); NAALADase inhibitors useful as pharmaceutical cpds. and compsns.. JP 2002519408; US 6395718; WO 0001668 .

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)	14738	Meldrum's acid; 2,2-dimethyl-1,3-dioxane-4,6-dione；Malonic acid cyclic isopropylidene ester	2033-24-1	C₆H₈O₄	详情	详情
(II)	63154	3-[(triphenylmethyl)sulfanyl]propanoic acid		C₂₂H₂₀O₂S	详情	详情
(III)	63155	5-{1-hydroxy-3-[(triphenylmethyl)sulfanyl]propylidene}-2,2-dimethyl-1,3-dioxane-4,6-dione		C₂₈H₂₆O₅S	详情	详情
(IV)	63156	2,2-dimethyl-5-{3-[(triphenylmethyl)sulfanyl]propyl}-1,3-dioxane-4,6-dione		C₂₈H₂₈O₄S	详情	详情
(V)	50285	3-Bromopropionic acid methyl ester; Methyl 3-bromopropionate	3395-91-3	C₄H₇BrO₂	详情	详情
(VI)	63157	methyl 3-(2,2-dimethyl-4,6-dioxo-5-{3-[(triphenylmethyl)sulfanyl]propyl}-1,3-dioxan-5-yl)propanoate		C₃₂H₃₄O₆S	详情	详情
(VII)	63158	6-[(triphenylmethyl)sulfanyl]-1,3,3-hexanetricarboxylic acid		C₂₈H₂₈O₆S	详情	详情
(VIII)	63159	2-{3-[(triphenylmethyl)sulfanyl]propyl}pentanedioic acid		C₂₇H₂₈O₄S	详情	详情

Extended Information