| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1345356 | Tetrahedron: Asymmetry | 2014 | 8 Pages |
Bicyclic azetidin-3-ones with no acidic α-hydrogens, prepared in good yields via cis-2,4-di-O-triflates of pyranosides, are stable divergent intermediates for the synthesis of highly substituted azetidines, as illustrated by the synthesis of (2R,3R,4R)-3-hydroxy-4-(hydroxymethyl)-3-methylazetidine-2-carboxylic acids. Preliminary studies on the reactions of bicyclic azetidinones indicate their potential as scaffolds for novel complex azetidines.
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Methyl 3-O-benzyl-N-butyl-2,4-dideoxy-2,4-imino-6-O-trityl-β-d-talopyranosideC37H41NO4[α]D20=-16.7 (c 0.50, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (2S,3S,4R,5S)
Methyl N-butyl-2,4-dideoxy-2,4-imino-6-O-trityl-β-d-lyxo-hexopyranoside-3-uloseC30H33NO4[α]D20=-43.2 (c 0.47, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (2R,4S,5S)
Methyl N-butyl-2,4-dideoxy-2,4-imino-3-methyl-6-O-trityl-β-d-talopyranosideC31H37NO4[α]D20=-50.1 (c 0.40, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (2S,3S,4S,5S)
Methyl 3-O-benzyl-N-butyl-2,4-dideoxy-2,4-imino-3-methyl-6-O-trityl-β-d-talopyranosideC38H43NO4[α]D20=-34.3 (c 0.44, CH2Cl2)Source of chirality: d-glucoseAbsolute configuration: (2S,3S,4S,5S)
1,5,6-Tri-O-acetyl-3-O-benzyl-N-butyl-2,4-dideoxy-2,4-imino-3-methyl-d-talitolC24H35NO7[α]D20=+24.2 (c 0.63, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (2R,3R,4S,5S)
Methyl 3-O-benzyl-N-butyl-2,4-dideoxy-2,4-imino-3-methyl-d-ribonateC18H27NO4[α]D20=-3.5 (c 0.46, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (2R,3R,4R)
3-O-Benzyl-N-butyl-2,4-dideoxy-2,4-imino-3-methyl-d-ribonic acidC17H25NO4[α]D20=-8.8 (c 0.25, methanol)Source of chirality: d-glucoseAbsolute configuration: (2R,3R,4R)
N-Butyl-2,4-dideoxy-2,4-imino-3-methyl-d-ribonic acidC10H19NO4[α]D20=+7.0 (c 0.60, methanol)Source of chirality: d-glucoseAbsolute configuration: (2R,3R,4R)
Methyl N-benzyl-2,4-dideoxy-2,4-imino-6-O-trityl-β-d-talopyranosideC33H33NO4[α]D20=-29.8 (c 0.40, methanol)Source of chirality: d-glucoseAbsolute configuration: (2S,3S,4R,5S)
Methyl N-benzyl-2,4-dideoxy-2,4-imino-6-O-trityl-β-d-lyxo-hexopyranoside-3-uloseC33H31NO4[α]D20=-55.4 (c 0.26, CH2Cl2)Source of chirality: d-glucoseAbsolute configuration: (2R,4S,5S)
Methyl N-benzyl-2,4-dideoxy-2,4-imino-3-methyl-6-O-trityl-β-d-talopyranosideC34H35NO4[α]D20=-48.5 (c 0.70, CH2Cl2)Source of chirality: d-glucoseAbsolute configuration: (2S,3S,4S,5S)
Methyl N-benzyl-3-O-benzyl-2,4-dideoxy-2,4-imino-3-methyl-6-O-trityl-β-d-talopyranosideC41H41NO4[α]D20=-40.7 (c 0.41, CH2Cl2)Source of chirality: d-glucoseAbsolute configuration: (2S,3S,4S,5S)
1,5,6-Tri-O-acetyl-N-benzyl-3-O-benzyl-2,4-dideoxy-2,4-imino-3-methyl-d-talitolC27H33NO7[α]D20=+38.4 (c 0.31, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (2R,3R,4S,5S)
Methyl N-benzyl-3-O-benzyl-2,4-dideoxy-2,4-imino-3-methyl-d-ribonateC21H25NO4[α]D20=+28.6 (c 0.40, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (2R,3R,4R)
N-Benzyl-3-O-benzyl-2,4-dideoxy-2,4-imino-3-methyl-d-ribonic acidC20H23NO4[α]D20=-6.4 (c 0.53, methanol)Source of chirality: d-glucoseAbsolute configuration: (2R,3R,4R)
2,4-Dideoxy-2,4-imino-3-methyl-d-ribonic acidC6H11NO4[α]D20=+8.4 (c 0.50, methanol)Source of chirality: d-glucoseAbsolute configuration: (2R,3R,4R)
Methyl N-butyl-2,3,4-trideoxy-2,4-imino-3-methyloxycarbonylmethyl-6-O-trityl-β-d-idopyranosideC33H39NO5[α]D20=-32.4 (c 0.53, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (2S,3R,4R,5S)
Methyl N-butyl-2,4-dideoxy-2,4-imino-3-O-trifluoromethanesulfonyl-6-O-trityl-β-d-talopyranosideC31H34F3NO6S[α]D20=-27.1 (c 0.41, CH2Cl2)Source of chirality: d-glucoseAbsolute configuration: (2S,3S,4S,5S)
