2-[[(8R)-7-(acetamido)-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]propionic acid -Drug Synthesis Database

【结构式】

【分子编号】24670

【品名】2-[[(8R)-7-(acetamido)-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]propionic acid

【CA登记号】74842-55-0

【分子式】C₂₅H₂₉NO₈

【分子量】471.5072

【元素组成】C 63.68% H 6.2% N 2.97% O 27.15%

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：(VI)

The reaction of N-benzltoxycarbonyl-L-alanine succinimidyl ester (I) with o-glutamine (II) by means of triethylamine in THF water gives benzyloxycarbonyl-L-alanyl-o-glutamine (III), which is esterified with bromobutane and Cs2CO3 in DMF yielding the corresponding butyl ester (IV). Deprotection of (IV) by hydrogenation with H2 over Pd/C in acetic acid affords L-alanyl-D-glutamine n-butyl ester (V), which is condensed with 1-O-benzyl-4,6-O-benzylidene-N-acetylmuramic acid (VI) bv the mixed anhydride method affording 1-O-benzyl-4,6-O-benzylidene-N-acetylmuramyl-L-alanyl-o-glutamine n-butyl ester (VII). Finally, this compound is deprotected by hydrogenation with H2 over Pd/C as before.

参考文献中间体

合成目标

【1】 Florvall, L.; Ogren, S.O.; Potential neuroleptic agents. 2,6-dialkoxybenzamide derivatives with potent dopamine receptor blocking activities. J Med Chem 1982, 25, 11, 1280.
【2】 Lefrancier, P.; Parant, M.; Audibert, F.; Chedid, L.; Choay, J.; Lederer, E. (ANVAR (Agence Natl. Valor. Rech.)); Novel compounds of the muramyl peptide. DD 145274; EP 0006068; ES 481785; FR 2428051; JP 55000392; US 4693998 .
【3】 Castaner, J.; Prous, J.; Murabutide. Drugs Fut 1986, 11, 9, 750.

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)	28721	1-bromobutane	109-65-9	C₄H₉Br	详情	详情
(I)	24665	phenethyl 2-[(2,5-dioxo-1-pyrrolidinyl)oxy]-1-methyl-2-oxoethylcarbamate		C₁₆H₁₈N₂O₆	详情	详情
(II)	24666	glutamine；2,5-diamino-5-oxopentanoic acid		C₅H₁₀N₂O₃	详情	详情
(III)	24667	N(2)-(2-[[(phenethyloxy)carbonyl]amino]propanoyl)glutamine		C₁₇H₂₃N₃O₆	详情	详情
(IV)	24668	butyl 5-amino-5-oxo-2-[(2-[[(phenethyloxy)carbonyl]amino]propanoyl)amino]pentanoate		C₂₁H₃₁N₃O₆	详情	详情
(V)	24669	butyl 5-amino-2-[(2-aminopropanoyl)amino]-5-oxopentanoate		C₁₂H₂₃N₃O₄	详情	详情
(VI)	24670	2-[[(8R)-7-(acetamido)-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]propionic acid	74842-55-0	C₂₅H₂₉NO₈	详情	详情
(VII)	24671	butyl 2-([2-[(2-[[(8R)-7-(acetamido)-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]propanoyl)amino]propanoyl]amino)-5-amino-5-oxopentanoate		C₃₇H₅₀N₄O₁₁	详情	详情

Extended Information