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Synthesis of Lacto‐ N ‐neohexaose and Lacto‐ N ‐neooctaose Using the Dimethylmaleoyl Moiety as an Amino Protective Group
Author(s) -
E. Aly Mohamed R.,
Ibrahim ElSayed I.,
ElAshry ElSayed H. E.,
Schmidt Richard R.
Publication year - 2000
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(200001)2000:2<319::aid-ejoc319>3.0.co;2-v
Subject(s) - chemistry , tetrasaccharide , stereochemistry , moiety , glycosylation , glycosyl , acceptor , glycosyl donor , acetylation , cleavage (geology) , derivative (finance) , organic chemistry , biochemistry , polysaccharide , physics , geotechnical engineering , fracture (geology) , financial economics , engineering , economics , gene , condensed matter physics
The N ‐DMM‐Protected lactosamine derivative 2 was readily transformed into the corresponding glycosyl donor 4 and into acceptor 5 . A TMSOTf‐catalyzed glycosidation afforded the derived tetrasaccharide 6 which led to glycosyl donor 9 . Reaction of 9 with lactose derivative 10 as acceptor gave the desired hexasaccharide 11 . Cleavage of all protective groups and N ‐acetylation afforded the target molecule 1b (lacto‐ N ‐neohexaose). Glycosylation of acceptor 10 with donor 4 furnished tetrasaccharide 16 which, employing standard procedures, gave acceptor 18 . Glycosylation of 18 with donor 9 furnished, under standard conditions, octasaccharide 19 . Cleavage of all protective groups and N ‐acetylation afforded the target molecule 1c (lacto‐ N ‐neooctaose). Both 1b and 1c were obtained in good overall yields.