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【结 构 式】

【分子编号】63128

【品名】(2S,6R)-2-[(2R)-3-(benzyloxy)-2-methylpropyl]-6-ethoxy-3,6-dihydro-2H-pyran; benzyl (2R)-3-[(2S,6R)-6-ethoxy-3,6-dihydro-2H-pyran-2-yl]-2-methylpropyl ether

【CA登记号】

【 分 子 式 】C18H26O3

【 分 子 量 】290.40264

【元素组成】C 74.45% H 9.02% O 16.53%

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:(XXXI)

The reaction of the chiral diol (XXIV) first with MsCl and TEA, and then with NaCN gives the chiral butyronitrile (XXV), which is reduced with DIBAL in dichloromethane to yield the butyraldehyde (XXVI). The reaction of (XXVI) with allyl tributyl tin (XXVII), (S)-BINOL and Ti(OiPr)4 affords the secondary alcohol (XXVIII), which is condensed with acetal (XXIX) by means of PPTS to provide the diene (XXX). A ring closing metathesis reaction in (XXX) by means of a Ru catalyst gives the dihydropyran derivative (XXXI). Alternatively, the reaction of (XXVIII) with propenoyl chloride (XXXII) by means of TEA gives the diene (XXXIII), which is submitted to a ring closing metathesis reaction as before to yield the dihydropyranone (XXXIV). The reduction of (XXXIV) with DIBAL, followed by treatment with CSA and ethanol affords the dihydropyran derivative (XXXV). The reaction of both acetals (XXXI) or (XXXV) with CH2=CH-O-Tbdms (XXXVI) in the presence of Montmorillonite as Lewis acid, followed by a treatment with NaBH4 provides the dihydropyran (XXXVII) as a single isomer.

1 Ghosh, A.K.; Wang, Y.; Kim, J.T.; Total synthesis of microtubule-stabilizing agent (-)-laulimalide. J Org Chem 2001, 66, 26, 8973.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXIV) 63122 (2R)-3-(benzyloxy)-2-methyl-1-propanol C11H16O2 详情 详情
(XXV) 63123 (3R)-4-(benzyloxy)-3-methylbutanenitrile C12H15NO 详情 详情
(XXVI) 63124 (3R)-4-(benzyloxy)-3-methylbutanal C12H16O2 详情 详情
(XXVII) 61128   C4H8 详情 详情
(XXVIII) 63125 (4S,6R)-7-(benzyloxy)-6-methyl-1-hepten-4-ol C15H22O2 详情 详情
(XXIX) 63126 3,3-diethoxy-1-propene; 1-ethoxy-2-propenyl ethyl ether C7H14O2 详情 详情
(XXX) 63127 1-[({(2R,4S)-4-[(1-ethoxy-2-propenyl)oxy]-2-methyl-6-heptenyl}oxy)methyl]benzene; benzyl (2R,4S)-4-[(1-ethoxy-2-propenyl)oxy]-2-methyl-6-heptenyl ether C20H30O3 详情 详情
(XXXI) 63128 (2S,6R)-2-[(2R)-3-(benzyloxy)-2-methylpropyl]-6-ethoxy-3,6-dihydro-2H-pyran; benzyl (2R)-3-[(2S,6R)-6-ethoxy-3,6-dihydro-2H-pyran-2-yl]-2-methylpropyl ether C18H26O3 详情 详情
(XXXII) 11577 Acryloyl chloride; Acrylyl chloride;2-Propenoyl chloride 814-68-6 C3H3ClO 详情 详情
(XXXIII) 63130 (1S)-1-[(2R)-3-(benzyloxy)-2-methylpropyl]-3-butenyl acrylate C18H24O3 详情 详情
(XXXIV) 63131 (6S)-6-[(2R)-3-(benzyloxy)-2-methylpropyl]-5,6-dihydro-2H-pyran-2-one C16H20O3 详情 详情
(XXXV) 63132 (2S,6S)-2-[(2R)-3-(benzyloxy)-2-methylpropyl]-6-ethoxy-3,6-dihydro-2H-pyran; benzyl (2R)-3-[(2S,6S)-6-ethoxy-3,6-dihydro-2H-pyran-2-yl]-2-methylpropyl ether C18H26O3 详情 详情
(XXXVI) 61133 tert-butyl(dimethyl)(vinyloxy)silane; tert-butyl(dimethyl)silyl vinyl ether C8H18OSi 详情 详情
(XXXVII) 63129 benzyl (2R)-3-[(2S,6R)-6-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3,6-dihydro-2H-pyran-2-yl]-2-methylpropyl ether; (2-{(2R,6S)-6-[(2R)-3-(benzyloxy)-2-methylpropyl]-5,6-dihydro-2H-pyran-2-yl}ethoxy)(tert-butyl)dimethylsilane C24H40O3Si 详情 详情
Extended Information