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Synthesis of L ‐Altrose and Some Derivatives
Author(s) -
Lunau Nathalie,
Meier Chris
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200938
Subject(s) - chemistry , mitsunobu reaction , epimer , derivative (finance) , stereochemistry , economics , financial economics
A convenient approach to the chemical synthesis of L ‐altrose ( 1 ) and its 6‐deoxy derivative 2 has been developed by starting from D ‐galactose ( 9 ) and D ‐fucose ( 10 ), respectively. The 5‐epimerization by a Mitsunobu inversion of the open‐chain D ‐hexoses was the key step for these routes. Furthermore, the conversion of 2 into peracetylated TDP‐6‐deoxy‐α‐ L ‐altrose ( 3a ) was achieved by the cyclo Sal approach. However, the final deacetylation led to an unexpected side‐reaction resulting in the previously unknown 6‐deoxy‐α‐ L ‐altropyranose 1,3‐cyclophosphate ( 4 ).