کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1348197 | 980344 | 2011 | 9 صفحه PDF | دانلود رایگان |

The synthesis of (4R,6S,7R)-7-hydroxy-4,6-dimethyl-3-nonanone and (3R,5S,6R)-6-hydroxy-3,5-dimethyl-2-octanone is described as their acetates using a desymmetrization strategy as well as an Evans syn aldol strategy.
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(3S,4R,5S,6S)-5-(Benzyloxy)-4,6-dimethylheptane-1,3,7-triolC16H26O4[α]D25=-6.9 (c 1.0, CHCl3)Absolute configuration: (3S,4R,5S,6S)Source of chirality: asymmetric synthesis
(2S,3S,4R)-3-(Benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxan-4-yl)-2-methylpentan-1-olC19H30O4[α]D25=+22.5 (c 1.5, CHCl3)Absolute configuration: (2S,3S,4R)-4-(S)Source of chirality: asymmetric synthesis
(S)-4-((2R,3S,4S)-3-(Benzyloxy)-5-(methoxymethoxy)-4-methylpentan-2-yl)-2,2-dimethyl-1,3-dioxaneC21H34O5[α]D25=-2.0 (c 0.5, CHCl3)Absolute configuration: (S)-4-(2R,3S,4S)Source of chirality: asymmetric synthesis
(2S,3S,4S)-4-((S)-2,2-Dimethyl-1,3-dioxan-4-yl)-1-(methoxymethoxy)-2-methylpentan-3-olC14H28O5[α]D25=-20.0 (c 0.5, CHCl3)Absolute configuration: (2S,3S,4S)-4-(S)Source of chirality: asymmetric synthesis
O-(2S,3S,4R)-4-((S)-2,2-Dimethyl-1,3-dioxan-4-yl)-1-(methoxymethoxy)-2-methylpentan-3-yl S-methyl carbonodithioateC16H30O5S2[α]D25=-9.0 (c 0.5, CHCl3)Absolute configuration: (2S,3S,4R)-4-(S)Source of chirality: asymmetric synthesis
(S)-4-((2S,4R)-5-(Methoxymethoxy)-4-methylpentan-2-yl)-2,2-dimethyl-1,3-dioxaneC14H28O4[α]D25=+5.5 (c 1.0, CHCl3)Absolute configuration: (S)-4-(2S,4R)Source of chirality: asymmetric synthesis
(3S,4S,6R)-7-(Methoxymethoxy)-4,6-dimethylheptane-1,3-diolC11H24O4[α]D25=-4.2 (c 1.5, CHCl3)Absolute configuration: (3S,4S,6R)Source of chirality: asymmetric synthesis
(3S,4S,6R)-3-Hydroxy-7-(methoxymethoxy)-4,6-dimethylheptyl 4-methylbenzenesulfonateC18H30O6S[α]D25=-21.0 (c 0.5, CHCl3)Absolute configuration: (3S,4S,6R)Source of chirality: asymmetric synthesis
(3S,4S,6R)-7-(Methoxymethoxy)-4,6-dimethylheptan-3-olC11H24O3[α]D25=-9.0 (c 1.0, CHCl3)Absolute configuration: (3S,4S,6R)Source of chirality: asymmetric synthesis
(((3S,4S,6R)-7-(Methoxymethoxy)-4,6-dimethylheptan-3-yloxy)methyl)benzeneC18H30O3[α]D25=-13.0 (c 0.5, CHCl3)Absolute configuration: (3S,4S,6R)Source of chirality: asymmetric synthesis
(2R,4S,5S)-5-(Benzyloxy)-2,4-dimethylheptan-1-olC16H26O2[α]D25=-1.8 (c 1.0, CHCl3)Absolute configuration: (2R,4S,5S)Source of chirality: asymmetric synthesis
(2R,3S)-1-((S)-4-Benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-2-methylpentan-1-oneC16H21NO2S2[α]D25=-32.5 (c 2.0, CHCl3)Absolute configuration: (2R,3S)-(S)-4Source of chirality: asymmetric synthesis
(2S,3S)-2-Methylpentane-1,3-diolC6H14O2[α]D25=+1.0 (c 0.5, CHCl3)Absolute configuration: (2S,3S)Source of chirality: asymmetric synthesis
(4S,5S)-4-Ethyl-5-methyl-2-phenyl-1,3-dioxaneC13H18O2[α]D25=-17.0 (c 0.5, CHCl3)Absolute configuration: (4S,5S)Source of chirality: asymmetric synthesis
(2S,3S)-3-(Benzyloxy)-2-methylpentan-1-olC13H20O2[α]D25=-2.0 (c 0.5, CHCl3)Absolute configuration: (2S,3S)Source of chirality: asymmetric synthesis
(2R,3S,4S,5S)-1-((S)-4-Benzyl-2-thioxothiazolidin-3-yl)-5-(benzyloxy)-3-hydroxy-2,4-dimethylheptan-1-oneC26H33NO3S2[α]D25=+41.0 (c 1.5, CHCl3)Absolute configuration: (2R,3S,4S,5S)-4-(S)Source of chirality: asymmetric synthesis
(2S,3R,4S,5S)-5-(Benzyloxy)-2,4-dimethylheptane-1,3-diolC16H26O3[α]D25=+21.1 (c 2.0, CHCl3)Absolute configuration: (2S,3R,4S,5S)Source of chirality: asymmetric synthesis
(2S,3R,4S,5S)-5-(Benzyloxy)-1-(tert-butyldimethylsilyloxy)-2,4-dimethylheptan-3-olC22H40O3Si[α]D25=+17.6 (c 1.0, CHCl3)Absolute configuration: (2S,3R,4S,5S)Source of chirality: asymmetric synthes
O-(2S,3R,4R,5S)-5-(Benzyloxy)-1-(tert-butyldimethylsilyloxy)-2,4-dimethylheptan-3-yl S-methyl carbonodithioateC24H42O3S2Si[α]D25=+5.1 (c 1.0, CHCl3)Absolute configuration: (2S,3R,4R,5S)Source of chirality: asymmetric synthesis
((2R,4S,5S)-5-(Benzyloxy)- 2,4-dimethylheptyloxy)(tert-butyl)dimethylsilaneC22H40O2Si[α]D25=+4.1 (c 1.0, CHCl3)Absolute configuration: (2R,4S,5S)Source of chirality: asymmetric synthesis
(4R,6S,7S)-7-(Benzyloxy)-4,6-dimethylnonan-3-oneC18H28O2[α]D25=-18.0 (c 0.5, CHCl3)Absolute configuration: (4R,6S,7S)Source of chirality: asymmetric synthesis
(3S,4S,6R)-4,6-Dimethyl-7-oxononan-3-yl acetateC13H24O3[α]D25=-4.8 (c 1.0, CHCl3)Absolute configuration: (3S,4S,6R)Source of chirality: asymmetric synthesis
(3R,4S,6R)-4,6-Dimethyl-7-oxononan-3-yl acetateC13H24O3[α]D25=+12.5 (c 1.0, CHCl3)Absolute configuration: (3R,4S,6R)Source of chirality: asymmetric synthesis
(3R,5S,6S)-6-(Benzyloxy)-3,5-dimethyloctan-2-oneC17H26O2[α]D25=-35.0 (c 0.5, CHCl3)Absolute configuration: (3R,5S,6S)Source of chirality: asymmetric synthesis
(3S,4S,6R)-4,6-Dimethyl-7-oxooctan-3-yl acetateC12H22O3[α]D25=-30.1 (c 1.0, CHCl3)Absolute configuration: (3S,4S,6R)Source of chirality: asymmetric synthesis
(3R,4S,6R)-4,6-Dimethyl-7-oxooctan-3-yl acetateC12H22O3[α]D25=-19.8 (c 1.0, CHCl3)Absolute configuration: (3R,4S,6R)Source of chirality: asymmetric synthesis
Journal: Tetrahedron: Asymmetry - Volume 22, Issue 24, 31 December 2011, Pages 2071–2079