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Chiral objects with a dendritic architecture
Author(s) -
Peerlings H.W.I.,
Struijk M.P.,
Meijer E.W
Publication year - 1998
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.9
Subject(s) - chemistry , chirality (physics) , enantiomer , macromolecule , stereochemistry , degeneracy (biology) , propane , molecule , organic chemistry , bioinformatics , biochemistry , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , biology , quark
The synthesis and characterization of both enantiomers of 2‐(benzyloxy)‐1‐ [3,5‐bis[[3,5‐bis(benzyloxy)]benzyloxy]benzyloxy]‐3‐[[3,5‐bis(benzyloxy)]benzyloxy] propane ( S‐7 and R‐7 ) are described. The chirality is based on the linkage of three constitutionally different, but chemically similar, dendritic wedges with a chiral glycerol derived core. Both enantiomers are synthesized from the same starting material: S‐(+)‐Solketal. Despite their enantiomeric purity, S‐7 and R‐7 lack any optical activity and may be regarded as the first macromolecular analogues of the well‐known organic molecules with “accidental degeneracy” or “cryptochirality.” Chirality 10:46–52, 1998. © 1998 Wiley‐Liss,Inc.