| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346740 | Tetrahedron: Asymmetry | 2010 | 7 Pages |
Four isomeric hydroxy-skipped bishomo-inositol analogs have been synthesized from both enantiomers of 5-hydroxymethyl-2-cyclohexenone. Sharpless asymmetric dihydroxylation and substrate-directed anionic hydroxymethylation are the key reactions which have been employed successfully for the synthesis of new cyclitols. The synthesized cyclitols have been screened for their inhibitory effect on α- and β-glycosidases.
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(5S,6S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-6-hydroxymethyl-cyclohex-2-enoneC24H30O3Si[α]D28=+17.0 (c 1.0, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (5S,6S)
(2S,3S,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5,6-dihydroxy-2-hydroxymethyl-cyclohexanoneC24H32O5Si[α]D28=+27.3 (c 1.0, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (2S,3S,5S,6S)
(1S,2S,3S,4S,5S)-4,5-Bis-hydroxymethyl-cyclohexane-1,2,3-triolC8H16O5[α]D28=+66.8 (c 1.0, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (1S,2S,3S,4S,5S)
(S)-5-(4-Methoxy-benzyloxymethyl)-cyclohex-2-enoneC15H18O3[α]D28=+7.25 (c 1.0, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (5S)
(5S,6S)-6-Hydroxymethyl-5-(4-methoxy-benzyloxymethyl)-cyclohex-2-enoneC16H20O4[α]D28=+14.5 (c 1.0, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (5S,6S)
(5S,6S)-6-(tert-Butyl-phenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxymethyl)-cyclohex-2-enoneC32H38O4Si[α]D28=+33.3 (c 1.0, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (5S,6S)
(5S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxymethyl-cyclohex-2-enoneC24H30O3Si[α]D28=+11.25 (c 1.0, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (5S,6S)
(2S,3S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5,6-dihydroxy-3-hydroxymethyl-cyclohexanoneC24H32O5Si[α]D28=+6.1 (c 1.0, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (2S,3S,5R,6R)
(1R,2R,3R,4S,5S)-4,5-Bis-hydroxymethyl-cyclohexane-1,2,3-triolC8H16O5[α]D28=+97.1 (c 1.0, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (1R,2R,3R,4S,5S)
(1R,2R,3R,4R,5R)-4,5-Bis-hydroxymethyl-cyclohexane-1,2,3-triolC8H16O5[α]D28=-66.2 (c 1.0, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (1R,2R,3R,4R,5R)
(1S,2S,3S,4R,5R)-4,5-Bis-hydroxymethyl-cyclohexane-1,2,3-triolC8H16O5[α]D28=-113.0 (c 1.0, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (1S,2S,3S,4R,5R)
