| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1344034 | Tetrahedron: Asymmetry | 2012 | 5 Pages |
Starting from carbohydrate precursors, hetero foldamer building blocks featuring diverse amino acid side chains and stereochemistry have been accessed via a multi-step synthetic protocol. These conformationally restricted bicyclic dipeptide building blocks are characterized by a constrained β-lactam ring fused with a pyrrolidine ring carrying a hydroxyethylamine isostere (HEA) on the backbone. These building blocks offer the possibility of developing foldamers with interesting structural architectures, conspicuously different from those classically observed. Furthermore, such hetero-building blocks have the potential to augment the conformational space available for foldamer design with diverse backbone conformations and structural architectures.
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(S)-Methyl 2-((2R,3R)-3-azido-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-oxoazetidin-1-yl)propanoateC12H18N4O5[α]D25=+160 (c 1, CHCl3)Source of chirality: d-glyceraldehydeAbsolute configuration: (S,R,R,S)
(S)-Methyl 2-((2R,3R)-3-azido-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-oxoazetidin-1-yl)-3-methylbutanoateC14H22N4O5[α]D25=+118 (c 1.5, CHCl3)Source of chirality: d-glyceraldehydeAbsolute configuration: (S,R,R,S)
(S)-Methyl 2-((2R,3R)-3-azido-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-oxoazetidin-1-yl)-4-methylpentanoateC15H24N4O5[α]D25=+146 (c 1, CHCl3)Source of chirality: d-glyceraldehydeAbsolute configuration: (S,R,R,S)
(R)-Methyl 2-((2R,3R)-3-azido-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-oxoazetidin-1-yl)-3-phenylpropanoateC18H22N4O5[α]D25=+170 (c 0.2, CHCl3)Source of chirality: d-glyceraldehydeAbsolute configuration: (R,R,R,S)
(S)-Methyl 2-((2R,3R)-3-azido-2-((S)-1,2-dihydroxyethyl)-4-oxoazetidin-1-yl)propanoateC9H14N4O5[α]D25=+164 (c 0.2, CHCl3)Source of chirality: d-glyceraldehydeAbsolute configuration: (S,R,R,S)
(S)-Methyl 2-((2R,3R)-3-azido-2-((S)-1,2-dihydroxyethyl)-4-oxoazetidin-1-yl)-3-methylbutanoateC11H18N4O5[α]D25=+100 (c 1, CHCl3)Source of chirality: d-glyceraldehydeAbsolute configuration: (S,R,R,S)
(S)-Methyl 2-((2R,3R)-3-azido-2-((S)-1,2-dihydroxyethyl)-4-oxoazetidin-1-yl)-4-methylpentanoateC12H20N4O5[α]D25=+150 (c 1, CHCl3)Source of chirality: d-glyceraldehydeAbsolute configuration: (S,R,R,S)
(R)-Methyl 2-((2R,3R)-3-azido-2-((S)-1,2-dihydroxyethyl)-4-oxoazetidin-1-yl)-3-phenylpropanoateC15H18N4O5[α]D25=+118 (c 1, CHCl3)Source of chirality: d-glyceraldehydeAbsolute configuration: (R,R,R,S)
(S)-Methyl 2-((2R,3R)-3-azido-2-((S)-1-hydroxy-2-(tosyloxy)ethyl)-4-oxoazetidin-1-yl)propanoateC16H20N4O7S[α]D25=+154 (c 1, CHCl3)Source of chirality: d-glyceraldehydeAbsolute configuration: (S,R,R,S)
(S)-Methyl 2-((2R,3R)-3-azido-2-((S)-1-hydroxy-2-(tosyloxy)ethyl)-4-oxoazetidin-1-yl)-3-methylbutanoateC18H24N4O7S[α]D25=+96 (c 1, CHCl3)Source of chirality: d-glyceraldehydeAbsolute configuration: (S,R,R,S)
(S)-Methyl 2-((2R,3R)-3-azido-2-((S)-1-hydroxy-2-(tosyloxy)ethyl)-4-oxoazetidin-1-yl)-4-methylpentanoateC19H26N4O7S[α]D25=+112 (c 1, CHCl3)Source of chirality: d-glyceraldehydeAbsolute configuration: (S,R,R,S)
(R)-Methyl 2-((2R,3R)-3-azido-2-((S)-1-hydroxy-2-(tosyloxy)ethyl)-4-oxoazetidin-1-yl)-3-phenylpropanoateC22H24N4O7S[α]D25=+124 (c 1, CHCl3)Source of chirality: d-glyceraldehydeAbsolute configuration: (R,R,R,S)
(1R,4R,5R)-tert-Butyl 4-hydroxy-6-((S)-1-methoxy-1-oxopropan-2-yl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-2-carboxylateC14H22N2O6[α]D25=+180 (c 0.7, CHCl3)Source of chirality: d-glyceraldehydeAbsolute configuration: (S,R,R,R)
(1R,4R,5R)-tert-Butyl 4-hydroxy-6-((S)-1-methoxy-3-methyl-1-oxobutan-2-yl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-2-carboxylateC16H26N2O6[α]D25=+110 (c 1, CHCl3)Source of chirality: d-glyceraldehydeAbsolute configuration: (S,R,R,R)
(1R,4R,5R)-tert-Butyl 4-hydroxy-6-((S)-1-methoxy-4-methyl-1-oxopentan-2-yl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-2-carboxylateC17H28N2O6[α]D25=+125 (c 0.8, CHCl3)Source of chirality: d-glyceraldehydeAbsolute configuration: (S,R,R,R)
(1R,4R,5R)-tert-Butyl 4-hydroxy-6-((R)-1-methoxy-1-oxo-3-phenylpropan-2-yl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-2-carboxylateC20H26N2O6[α]D25=+190 (c 1, CHCl3)Source of chirality: d-glyceraldehydeAbsolute configuration: (R,R,R,R)
