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【结 构 式】

【分子编号】62116

【品名】(2S,3R,6R)-3,6-dimethyl-2-[4-(trimethylsilyl)-3-butynyl]-3,6-dihydro-2H-pyran-4-yl triethylsilyl ether; (4-{(2S,3R,6R)-3,6-dimethyl-4-[(triethylsilyl)oxy]-3,6-dihydro-2H-pyran-2-yl}-1-butynyl)(trimethyl)silane

【CA登记号】

【 分 子 式 】C20H38O2Si2

【 分 子 量 】366.69152

【元素组成】C 65.51% H 10.45% O 8.73% Si 15.32%

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:(VIII)

Hetero Diels-Alder reaction between diene (VI) and aldehyde (VII) in the presence of chiral chromium complex furnishes the optically active dihydropyran compound (VIII). Subsequent oxidation of the silyl enol ether moiety of (VIII) with m CPBA under Rubottom conditions affords the alpha-hydroxy ketone (IX). Reduction of ketone (IX) is accomplished via the tosyl hydrazone (X), which is then reduced to (XI) employing NaBH3CN. Desilylation of (XI) with tetrabutylammonium fluoride gives the terminal acetylene (XII), which is further isomerized to the thermodynamically more stable internal alkyne (XIII) in the presence of potassium tert-butoxide in DMSO. Treatment of (XIII) with Schwartz's reagent, followed by quenching of the vinylzirconium intermediate with I2 leads to the vinyl iodide (XIV). After conversion of alcohol (XIV) into the chloromethanesulfonate (XV), displacement with LiN3 provides azide (XVI).

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
(VI) 62114 triethyl({(E)-1-[(Z)ethylidene]-2-butenyl}oxy)silane; (E)-1-[(Z)ethylidene]-2-butenyl triethylsilyl ether C12H24OSi 详情 详情
(VII) 62115 5-(trimethylsilyl)-4-pentynal C8H14OSi 详情 详情
(VIII) 62116 (2S,3R,6R)-3,6-dimethyl-2-[4-(trimethylsilyl)-3-butynyl]-3,6-dihydro-2H-pyran-4-yl triethylsilyl ether; (4-{(2S,3R,6R)-3,6-dimethyl-4-[(triethylsilyl)oxy]-3,6-dihydro-2H-pyran-2-yl}-1-butynyl)(trimethyl)silane C20H38O2Si2 详情 详情
(IX) 62117 (2R,3R,5R,6S)-3-hydroxy-2,5-dimethyl-6-[4-(trimethylsilyl)-3-butynyl]tetrahydro-4H-pyran-4-one C14H24O3Si 详情 详情
(X) 62118 N'-{(2R,3S,5S,6S)-3-hydroxy-2,5-dimethyl-6-[4-(trimethylsilyl)-3-butynyl]tetrahydro-4H-pyran-4-ylidene}-4-methylbenzenesulfonohydrazide C21H32N2O4SSi 详情 详情
(XI) 62119 (2R,3S,5S,6S)-2,5-dimethyl-6-[4-(trimethylsilyl)-3-butynyl]tetrahydro-2H-pyran-3-ol C14H26O2Si 详情 详情
(XII) 62120 (2R,3S,5S,6S)-6-(3-butynyl)-2,5-dimethyltetrahydro-2H-pyran-3-ol C11H18O2 详情 详情
(XIII) 62121 (2R,3S,5S,6S)-6-(2-butynyl)-2,5-dimethyltetrahydro-2H-pyran-3-ol C11H18O2 详情 详情
(XIV) 62122 (2R,3S,5S,6S)-6-[(E)-3-iodo-2-butenyl]-2,5-dimethyltetrahydro-2H-pyran-3-ol C11H19IO2 详情 详情
(XV) 62123 (2R,3S,5S,6S)-6-[(E)-3-iodo-2-butenyl]-2,5-dimethyltetrahydro-2H-pyran-3-yl chloromethanesulfonate C12H20ClIO4S 详情 详情
(XVI) 62124 (2R,3R,5S,6S)-6-[(E)-3-iodo-2-butenyl]-2,5-dimethyltetrahydro-2H-pyran-3-yl azide; (2R,3R,5S,6S)-3-azido-6-[(E)-3-iodo-2-butenyl]-2,5-dimethyltetrahydro-2H-pyran C11H18IN3O 详情 详情
Extended Information