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【结 构 式】 
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【分子编号】58132 【品名】(3R,4R,5S,6R)-5-[((2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}tetrahydro-2H-pyran-2-yl)oxy]-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4-triol; D-(+)-Maltotriose; D-Maltotriose; Maltotriose; O-alpha-D-Glucopyranosyl-(1->4)-O-alpha-D-glucopyranosyl-(1->4 )-D-glucose 【CA登记号】1109-28-0 |
【 分 子 式 】C18H32O16 【 分 子 量 】504.44248 【元素组成】C 42.86% H 6.39% O 50.75% |
合成路线1
该中间体在本合成路线中的序号：(I)The intermediate thioglycoside (V) is prepared as follows. Esterification of maltotriose (I) with acetic anhydride and sodium acetate provides peracetate (II). Subsequent reaction of (II) with ethanethiol in the presence of boron trifluoride etherate yields the ethyl thiopyranoside (III). Removal of the acetate esters of (III) is effected by methanolysis in the presence of potassium tert-butoxide, yielding (IV). Then, reesterification of (IV) by means of benzoyl chloride and pyridine furnishes the target intermediate (V).
| 【1】 Petitou, M.; Herbert, J.-M.; Duchaussoy, P.; Basten, J.; Dreef-Tromp, C.; Driguez, P.-A.; Van Boeckel, C. (Akzo Nobel N.V.; Sanofi-Synthélabo); Synthetic polysaccharides, their method of production and pharmaceutical compsns. containing same. EP 1049721; FR 2773804; US 6528497; WO 9936443 . |
| 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) | 58132 | (3R,4R,5S,6R)-5-[((2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}tetrahydro-2H-pyran-2-yl)oxy]-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4-triol; D-(+)-Maltotriose; D-Maltotriose; Maltotriose; O-alpha-D-Glucopyranosyl-(1->4)-O-alpha-D-glucopyranosyl-(1->4 )-D-glucose | 1109-28-0 | C18H32O16 | 详情 | 详情 |
| (II) | 58133 | (2R,3R,4S,5R,6R)-3-(acetyloxy)-6-[(acetyloxy)methyl]-5-({(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl}oxy)-2-({(2R,3R,4S,5R,6S)-4,5,6-tris(acetyloxy)-2-[(acetyloxy)methyl]tetrahydro-2H-pyran-3-yl}oxy)tetrahydro-2H-pyran-4-yl acetate | C40H54O27 | 详情 | 详情 | |
| (III) | 58134 | (2R,3R,4S,5R,6R)-3-(acetyloxy)-6-[(acetyloxy)methyl]-2-{[(2R,3S,4S,5R,6S)-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]-6-(ethylsulfanyl)tetrahydro-2H-pyran-3-yl]oxy}-5-({(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl}oxy)tetrahydro-2H-pyran-4-yl acetate | C40H56O25S | 详情 | 详情 | |
| (IV) | 58135 | (2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6S)-6-(ethylsulfanyl)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol | C20H36O15S | 详情 | 详情 | |
| (V) | 58136 | (2S,3R,4S,5S,6R)-3-(benzoyloxy)-6-[(benzoyloxy)methyl]-5-{[(2R,3R,4S,5R,6R)-3,4-bis(benzoyloxy)-6-[(benzoyloxy)methyl]-5-({(2R,3R,4S,5R,6R)-3,4,5-tris(benzoyloxy)-6-[(benzoyloxy)methyl]tetrahydro-2H-pyran-2-yl}oxy)tetrahydro-2H-pyran-2-yl]oxy}-2-(ethylsulfanyl)tetrahydro-2H-pyran-4-yl benzoate | C90H76O25S | 详情 | 详情 |