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Chirale Bausteine aus Kohlenhydraten, XIV. Umsetzung von 6‐Desoxy‐6‐iod‐1,2;3,4‐di‐ O ‐isopropyliden‐α‐ D ‐galactopyranose mit 2‐Lithio‐1,3‐dithian zu offenkettigen Heptosederivaten
Author(s) -
Redlich Hartmut,
Lenfers Jan Bernd
Publication year - 1988
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198819880619
Subject(s) - chemistry , heptose , chirality (physics) , stereochemistry , medicinal chemistry , physics , biochemistry , chiral symmetry breaking , quantum mechanics , mutant , nambu–jona lasinio model , gene , quark
Chiral Building Units from Carbohydrates, XIV. – 2‐Lithio‐1,3‐dithiane‐Induced Transformation of 6‐Deoxy‐6‐iodo‐1,2;3,4‐di‐ O ‐isopropylidene‐α‐ D ‐galactopyranose into Open‐Chain Heptose Derivatives The reaction of 6‐deoxy‐6‐iodo‐1,2;3,4‐di‐ O ‐isopropylidene‐α‐ D ‐galactopyranose ( 1 ) with 2‐lithio‐1,3‐dithiane ( 2 ) and 4,5‐dihydro‐2‐lithio‐5‐methyl‐1,3,5‐dithiazin ( 3 ) yields the unsaturated open‐chain heptose derivatives 4a, 4d , and 5a . The selectivity concerning the newly formed chirality center at C‐2 is in the ratio of 3:1.