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【结 构 式】

【分子编号】56333

【品名】methyl (2R)-2-[((1R,2R)-2-(acetylamino)-1-{(S)-({(2S,3R,4R,5S,6R)-3-(acetylamino)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-yl}oxy)[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-3,3-diethoxypropyl)oxy]propanoate

【CA登记号】

【 分 子 式 】C48H66N2O14

【 分 子 量 】895.05712

【元素组成】C 64.41% H 7.43% N 3.13% O 25.03%

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:(XII)

Alkylation of the sodium alkoxide of (X) with (S)-2-chloropropionic acid (XI), followed by esterification with diazomethane provided the methyl ester adduct (XII). Alkaline hydrolysis of ester (XII) with KOH yielded carboxylic acid (XIII), which was coupled with the dipeptide amide (XIV) to give the protected disaccharide dipeptide (XV). Subsequent acidic hydrolysis of the ketal functions of (XV) proceeded with concomitant cyclization to the pyranose form (XVI). The O-benzyl protecting groups of (XVI) were finally removed by catalytic hydrogenolysis in the presence of palladium black.

1 Kusumoto, S.; et al.; Synthesis of N-acetyl-beta-D-glucosaminyl-(1-4)-N-acetylmuramyl-L-alanyl-D-isoglutamine. Tetrahedron Lett 1978, 45, 4407.
2 Kusumoto, S.; et al.; Chemical synthesis and biological activities of two disaccharide dipeptides corresponding to the repeating units of bacterial peptidoglycan. Bull Chem Soc Jpn 1986, 59, 5, 1411.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(X) 56331 N-{(1R,2R,3S)-3-({(2S,3R,4R,5S,6R)-3-(acetylamino)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-yl}oxy)-1-(diethoxymethyl)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxypropyl}acetamide C44H60N2O12 详情 详情
(XI) 56332 (S)-(-)-2-Chloropropionic acid; (S)-2-Chloropropionic acid 29617-66-1 C3H5ClO2 详情 详情
(XII) 56333 methyl (2R)-2-[((1R,2R)-2-(acetylamino)-1-{(S)-({(2S,3R,4R,5S,6R)-3-(acetylamino)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-yl}oxy)[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-3,3-diethoxypropyl)oxy]propanoate C48H66N2O14 详情 详情
(XIII) 56334 (2R)-2-[((1R,2R)-2-(acetylamino)-1-{(S)-({(2S,3R,4R,5S,6R)-3-(acetylamino)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-yl}oxy)[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-3,3-diethoxypropyl)oxy]propanoic acid C47H64N2O14 详情 详情
(XIV) 27130 benzyl (4R)-5-amino-4-[[(2S)-2-aminopropanoyl]amino]-5-oxopentanoate C15H21N3O4 详情 详情
(XV) 56335 benzyl (5R,6R,8R,11S,14R)-5-(acetylamino)-6-{(S)-({(2S,3R,4R,5S,6R)-3-(acetylamino)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-yl}oxy)[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-14-(aminocarbonyl)-4-ethoxy-8,11-dimethyl-9,12-dioxo-3,7-dioxa-10,13-diazaheptadecan-17-oate C62H83N5O17 详情 详情
(XVI) 56336 benzyl (4R)-4-({(2S)-2-[((2R)-2-{[(2S,3R,4R,5S,6R)-3-(acetylamino)-5-({(2S,3R,4R,5S,6R)-3-(acetylamino)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-yl}oxy)-2-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl]oxy}propanoyl)amino]propanoyl}amino)-5-amino-5-oxopentanoate C55H69N5O16 详情 详情
Extended Information