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A Novel and Efficient Route towards α‐GalNAc‐Ser and α‐GalNAc‐Thr Building Blocks for Glycopeptide Synthesis
Author(s) -
Winterfeld Gottfried A.,
Ito Yukishige,
Ogawa Tomoya,
Schmidt Richard R.
Publication year - 1999
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(199905)1999:5<1167::aid-ejoc1167>3.0.co;2-2
Subject(s) - chemistry , glycopeptide , threonine , stereoselectivity , serine , nitro , stereochemistry , yield (engineering) , protecting group , raney nickel , combinatorial chemistry , catalysis , organic chemistry , biochemistry , antibiotics , enzyme , alkyl , materials science , metallurgy
Michael addition of serine and threonine derivatives 4a – 4c to 3,4,6‐tri‐ O ‐benzyl‐2‐nitro‐ D ‐galactal ( 1 ) afforded the corresponding 2‐deoxy‐2‐nitro‐α‐ D ‐galactopyranosides 5a–5c in good yield and stereoselectivity. 2‐deoxy‐2‐nitroglycosides 5a and 5b were reduced to the 2‐acetamido compounds by platinized Raney nickel T4. Manipulation of the protecting groups afforded known N ‐Fmoc‐ O ‐(2‐acetamido‐3,4,6‐tri‐ O ‐acetyl‐2‐deoxy‐α‐ D ‐galactopyranosyl)‐ L ‐serine ( 8a ) and ‐threonine ( 8b ), valuable building blocks for O ‐glycopeptide synthesis.