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Enantiopure D‐, L‐ (and 2‐ epi ‐) Purpurosamine C‐Type Glycosyl Donors from Racemic Acrolein Dimer − Biocatalytic Resolution
Author(s) -
Erbeck Silke,
Liang Xifu,
Krieger Richard,
Prinzbach Horst
Publication year - 1998
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/(sici)1099-0690(199803)1998:3<481::aid-ejoc481>3.0.co;2-z
Subject(s) - chemistry , enantiopure drug , acrolein , dimer , enantiomer , epimer , stereochemistry , glycosyl donor , glycosyl , resolution (logic) , enantioselective synthesis , organic chemistry , catalysis , artificial intelligence , computer science
Both enantiomers of purpurosamine C‐type glycosyl donors [( ent )‐ 9 , ( ent )‐ 10 , ( ent )‐ 11 ] and of a 2‐azido epimer [( ent )‐ 14 ] with a modified pattern of protecting groups have been prepared from racemic 3,4‐dihydro‐2 H ‐pyran‐2‐carbaldehyde (acrolein dimer, rac ‐ 1 , “indirect aziridination”, “azidonitration”). In two cases ( rac ‐ 23β : methyl 6‐ O ‐acetyl‐2,3,4‐trideoxy‐2α‐trifluoroacetylamino‐β‐D/L‐hexopyranoside, rac ‐ 32 : methyl 6‐ O ‐acetyl‐2β‐azido‐2,3,4‐trideoxy‐β‐D/L‐hexopyranoside), efficient resolution has been achieved biocatalytically.