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【结 构 式】

【分子编号】62139

【品名】(1S,2Z)-4-[((2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,4R,5R)-4-hydroxy-7-methylene-1,6-dioxaspiro[2.5]oct-5-yl]-3-methyl-2,4-pentadienyl}-2,5-dimethyltetrahydro-2H-pyran-3-yl)amino]-1-methyl-4-oxo-2-butenyl acetate

【CA登记号】

【 分 子 式 】C27H39NO7

【 分 子 量 】489.6092

【元素组成】C 66.24% H 8.03% N 2.86% O 22.87%

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:(XXXII)

Acylation of amine (XXIX) with the unsaturated acid (V) in the presence of HBTU gives amide (XXX). Dehydroiodination of (XXX) by means of DBU in DMF leads to the exocyclic enol ether (XXXI). The O-silyl group of (XXXI) is then removed with tetrabutylammonium fluoride and acetic acid, to yield alcohol (XXXII). Finally, acid-catalyzed hydration of the cyclic enol ether (XXXII) in aqueous THF gives rise to the target hemiketal compound.

1 Thompson, C.F.; Jamison, T.F; Jacobsen, E.N.; Total synthesis of FR901464. Convergent assembly of chiral componenents prepared by asymmetric catalysis. J Am Chem Soc 2000, 122, 45, 10482.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(V) 62113 (Z,4S)-4-(acetyloxy)-2-pentenoic acid C7H10O4 详情 详情
(XXIX) 62136 (2R,3R,5S,6S)-6-((2E,4E)-5-{(3R,4R,5R,7R)-7-(iodomethyl)-4-[(triethylsilyl)oxy]-1,6-dioxaspiro[2.5]oct-5-yl}-3-methyl-2,4-pentadienyl)-2,5-dimethyltetrahydro-2H-pyran-3-amine; (2R,3R,5S,6S)-6-((2E,4E)-5-{(3R,4R,5R,7R)-7-(iodomethyl)-4-[(triethylsilyl)oxy]-1,6-dioxaspiro[2.5]oct-5-yl}-3-methyl-2,4-pentadienyl)-2,5-dimethyltetrahydro-2H-pyran-3-ylamine C26H46INO4Si 详情 详情
(XXX) 62137 (1S,2Z)-4-{[(2R,3R,5S,6S)-6-((2E,4E)-5-{(3R,4R,5R,7R)-7-(iodomethyl)-4-[(triethylsilyl)oxy]-1,6-dioxaspiro[2.5]oct-5-yl}-3-methyl-2,4-pentadienyl)-2,5-dimethyltetrahydro-2H-pyran-3-yl]amino}-1-methyl-4-oxo-2-butenyl acetate C33H54INO7Si 详情 详情
(XXXI) 62138 (1S,2Z)-4-{[(2R,3R,5S,6S)-2,5-dimethyl-6-((2E,4E)-3-methyl-5-{(3R,4R,5R)-7-methylene-4-[(triethylsilyl)oxy]-1,6-dioxaspiro[2.5]oct-5-yl}-2,4-pentadienyl)tetrahydro-2H-pyran-3-yl]amino}-1-methyl-4-oxo-2-butenyl acetate C33H53NO7Si 详情 详情
(XXXII) 62139 (1S,2Z)-4-[((2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,4R,5R)-4-hydroxy-7-methylene-1,6-dioxaspiro[2.5]oct-5-yl]-3-methyl-2,4-pentadienyl}-2,5-dimethyltetrahydro-2H-pyran-3-yl)amino]-1-methyl-4-oxo-2-butenyl acetate C27H39NO7 详情 详情
Extended Information