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【结 构 式】 
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【分子编号】20876 【品名】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 【CA登记号】 |
【 分 子 式 】C47H62N6O14 【 分 子 量 】935.04132 【元素组成】C 60.37% H 6.68% N 8.99% O 23.96% |
合成路线1
该中间体在本合成路线中的序号：(X)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 |
合成路线2
该中间体在本合成路线中的序号：(X)Hydrogenation of (X) with H2 over Pd/C in acetic acid affords Nalpha-(N-acetylmuramoyl-L-alanyl-D-isoglutaminyl)-L-lysine (XI), which is finally condensed with N-hydroxynorbornene-2,3-dicarboxyimide ester of stearic acid (XII) by means of N-methylmorpholine in DMF.
| 【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 |
|---|---|---|---|---|---|---|
| 28928 | 4-methylmorpholine | 109-02-4 | C5H11NO | 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 | |
| (XI) | 20877 | N(2)-[4-([2-[(2-[[3-(acetamido)-2,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl]oxy]propanoyl)amino]propanoyl]amino)-5-amino-5-oxopentanoyl]lysine | C25H44N6O12 | 详情 | 详情 | |
| (XII) | 20878 | 4-(stearoyloxy)-4-azatricyclo[5.2.1.0(2,6)]dec-2(6)-ene-3,5-dione | C27H43NO4 | 详情 | 详情 |