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【结 构 式】

【分子编号】20873

【品名】benzyl 2-([5-amino-4-[(2-aminopropanoyl)amino]-5-oxopentanoyl]amino)-6-[[(benzyloxy)carbonyl]amino]hexanoate

【CA登记号】

【 分 子 式 】C29H39N5O7

【 分 子 量 】569.65816

【元素组成】C 61.15% H 6.9% N 12.29% O 19.66%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(VII)

The condensation of tert-butoxycarbonyl-L-alanine (I) with benzyl D-isoglutaminate (II) by means of N-hydroxysuccinimide (NOHS) and dicyclohexylcarbodiimide (DCC) gives the protected dipeptide (III), which is hydrogenated with H2 over Pd/C in methanol yielding tert-butoxycarbonyl-D-isoglutaminyl-L-alanine (IV). The condensation of (IV) with Nepsilon-(benzyloxycarbonyl)-L-lysine benzyl ester (V) by means of ethyl chloroformate and triethylamine affords the protected tripeptide (VI), which is treated with trifluoroacetic acid (TFA) to afford L-alanyl-D-isoglutaminyl-(Nepsilon-benzyloxycarbonyl)-L-lysine benzyl ester (VII).

1 Shiba, T.; Yamamura, Y.; Nagase, O.; Kotani, S.; Ogawa, H. (Daiichi Seiyaku Co.; Ltd.); Muramyldipeptide derivatives, process for preparing said compounds and pharmaceutical compositions containing said compounds. EP 0021367 .
2 Robinson, C.P.; MUROCTASIN. Drugs Fut 1989, 14, 5, 432.
3 Shiba, T.; Kusumoto, S.; Tarumi, Y.; Ikenaka, K.; Chemical synthesis of N-acetylmuramyl peptides with partial structures of bacterial cell wall and their analogs in relation to immunoadjuvant activities. 1976, 49(2): 533-9. Bull Chem Soc Jpn 1976, 49, 2, 533.
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) 20337 N-(tert-butoxycarbonyl)alanine C8H15NO4 详情 详情
(II) 20868 benzyl 4,5-diamino-5-oxopentanoate C12H16N2O3 详情 详情
(III) 20869 benzyl 5-amino-4-([2-[(tert-butoxycarbonyl)amino]propanoyl]amino)-5-oxopentanoate C20H29N3O6 详情 详情
(IV) 20870 5-amino-4-([2-[(tert-butoxycarbonyl)amino]propanoyl]amino)-5-oxopentanoic acid C13H23N3O6 详情 详情
(V) 20871 benzyl 2-amino-6-[[(benzyloxy)carbonyl]amino]hexanoate C21H26N2O4 详情 详情
(VI) 20872 benzyl 9-(aminocarbonyl)-14-(4-[[(benzyloxy)carbonyl]amino]butyl)-2,2,6-trimethyl-4,7,12-trioxo-3-oxa-5,8,13-triazapentadecan-15-oate C34H47N5O9 详情 详情
(VII) 20873 benzyl 2-([5-amino-4-[(2-aminopropanoyl)amino]-5-oxopentanoyl]amino)-6-[[(benzyloxy)carbonyl]amino]hexanoate C29H39N5O7 详情 详情

合成路线2

该中间体在本合成路线中的序号:(VII)

The condensation of (VII) with 1-O-benzyl-4,6-O-benzylidene-N-acetylmuramic acid (VIII) by means of NOHS and DCC as before gives the protected muramyl tripeptide (IX) , which is treated with acetic acid yielding the partially protected compound (X).

1 Shiba, T.; Yamamura, Y.; Nagase, O.; Kotani, S.; Ogawa, H. (Daiichi Seiyaku Co.; Ltd.); Muramyldipeptide derivatives, process for preparing said compounds and pharmaceutical compositions containing said compounds. EP 0021367 .
2 Robinson, C.P.; MUROCTASIN. Drugs Fut 1989, 14, 5, 432.
3 Shiba, T.; Kusumoto, S.; Tarumi, Y.; Ikenaka, K.; Chemical synthesis of N-acetylmuramyl peptides with partial structures of bacterial cell wall and their analogs in relation to immunoadjuvant activities. 1976, 49(2): 533-9. Bull Chem Soc Jpn 1976, 49, 2, 533.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 20873 benzyl 2-([5-amino-4-[(2-aminopropanoyl)amino]-5-oxopentanoyl]amino)-6-[[(benzyloxy)carbonyl]amino]hexanoate C29H39N5O7 详情 详情
(VIII) 20874 2-[[7-(acetamido)-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]propionic acid C25H29NO8 详情 详情
(IX) 20875 benzyl 2-[[4-([2-[(2-[[7-(acetamido)-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]propanoyl)amino]propanoyl]amino)-5-amino-5-oxopentanoyl]amino]-6-[[(benzyloxy)carbonyl]amino]hexanoate C54H66N6O14 详情 详情
(X) 20876 benzyl 2-[[4-([2-[(2-[[3-(acetamido)-2-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl]oxy]propanoyl)amino]propanoyl]amino)-5-amino-5-oxopentanoyl]amino]-6-[[(benzyloxy)carbonyl]amino]hexanoate C47H62N6O14 详情 详情
Extended Information