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Conjugate Addition of Phenols to 2‐Nitrogalactal − Synthesis of O ‐(2‐Acetamido‐2‐deoxygalactosyl)tyrosine
Author(s) -
Khodair Ahmed I.,
Winterfeld Gottfried A.,
Schmidt Richard R.
Publication year - 2003
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.200200712
Subject(s) - chemistry , conjugate , phenols , tyrosine , phenol , derivative (finance) , nitro , aryl , catalysis , base (topology) , stereochemistry , medicinal chemistry , organic chemistry , biochemistry , financial economics , economics , mathematical analysis , alkyl , mathematics
2‐Nitrogalactal derivative 1 afforded 2‐deoxy‐2‐nitrogalactopyranosides on treatment with phenol and substituted derivatives under base catalysis. Transformation of the nitro group into the amino and the acetamido groups and O ‐deprotection could readily be performed, thus providing aryl 2‐acetamido‐2‐deoxygalactopyranosides 5 and 6 in high yields and with good stereoselectivities. The same reaction sequence could also be successfully applied to N ‐Boc‐protected tyrosine methyl ester, to afford the O ‐galactopyranonsyl tyrosine derivative 10 . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)