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【结 构 式】

【分子编号】21545

【品名】(2R,3R)-2-[[tert-butyl(dimethyl)silyl]oxy]-3-methoxy-3-methyl-1-heptanol

【CA登记号】

【 分 子 式 】C15H34O3Si

【 分 子 量 】290.51866

【元素组成】C 62.01% H 11.8% O 16.52% Si 9.67%

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:(XIX)

2) The epoxidation of nerol (XII) with tert-butyl peroxide and titanium isopropoxide gives the epoxide (XIII), which is benzylated with benzyl bromide to the protected epoxide (XIV). A stereo- and regioselective cleavage of the epoxide (XIV) with methanol yields the methoxy hydroxy derivative (XV), which is ozonolyzed in methanol dichloromethane to the aldehyde (XVI). The Wittig condensation of (XVI) with triphenylmethylphosphonium bromide and potassium tert-butoxide affords the methylene alcohol (XVII), which is protected with tert-butyldimethylsilyl chloride as before to give silyl derivative (XVIII). The hydrogenation of (XVIII) with H2 over Pd in ethyl acetate yields the saturated alcohol (XIX), which is oxidized with oxalyl chloride in DMSO to the aldehyde (XX).The reaction of (XX) with tetrabromomethane and triphenylphosphine affords the dibromovinyl compound (XXI), which by reaction with butyllithium in THF is converted into the acetylene (XXII). Finally, this compound is treated with tributylstannyl hydride and azobisisobutyronitrile to give the stannyl derivative (II).

1 Kolb, M.; Van Hijfte, L.; Ireland, R.E.; A highly convergent synthesis of mexiprostil: 16(R) 16-methoxy 16-methyl PGE1 methyl ester. Tetrahedron Lett 1988, 29, 51, 6769.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
30484 Methyl(triphenyl)phosphonium bromide 1779-49-3 C19H18BrP 详情 详情
(A) 12912 1-(Bromomethyl)benzene; Alpha-bromotoluene 100-39-0 C7H7Br 详情 详情
(II) 21528 (1R,2R,3E)-1-butyl-2-[[tert-butyl(dimethyl)silyl]oxy]-1-methyl-4-(tributylstannyl)-3-butenyl methyl ether C28H60O2SiSn 详情 详情
(XII) 21538 (2Z)-3,7-dimethyl-2,6-octadien-1-ol 106-25-2 C10H18O 详情 详情
(XIII) 21539 [(2R,3S)-3-methyl-3-(4-methyl-3-pentenyl)oxiranyl]methanol C10H18O2 详情 详情
(XIV) 21540 (2S,3R)-3-[(benzyloxy)methyl]-2-methyl-2-(4-methyl-3-pentenyl)oxirane C17H24O2 详情 详情
(XV) 21541 (2R,3R)-1-(benzyloxy)-3-methoxy-3,7-dimethyl-6-octen-2-ol C18H28O3 详情 详情
(XVI) 21542 (4R,5R)-6-(benzyloxy)-5-hydroxy-4-methoxy-4-methylhexanal C15H22O4 详情 详情
(XVII) 21543 (2R,3R)-1-(benzyloxy)-3-methoxy-3-methyl-6-hepten-2-ol C16H24O3 详情 详情
(XVIII) 21544 ([(1R,2R)-1-[(benzyloxy)methyl]-2-methoxy-2-methyl-5-hexenyl]oxy)(tert-butyl)dimethylsilane C22H38O3Si 详情 详情
(XIX) 21545 (2R,3R)-2-[[tert-butyl(dimethyl)silyl]oxy]-3-methoxy-3-methyl-1-heptanol C15H34O3Si 详情 详情
(XX) 21546 (3R,4R)-3-[[tert-butyl(dimethyl)silyl]oxy]-4-methoxy-4-methyloctanal C16H34O3Si 详情 详情
(XXI) 21547 tert-butyl(dimethyl)silyl (1R)-3,3-dibromo-1-[(1R)-1-methoxy-1-methylpentyl]-2-propenyl ether C16H32Br2O2Si 详情 详情
(XXII) 21548 (1R,2R)-1-butyl-2-[[tert-butyl(dimethyl)silyl]oxy]-1-methyl-3-butynyl methyl ether C16H32O2Si 详情 详情
Extended Information