Premium
Synthesis of Trisaccharides and Tetrasaccharides by Means of Intramolecular Glycosylation Supported by Rigid Spacers
Author(s) -
Müller Matthias,
Schmidt Richard R.
Publication year - 2001
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 - 10.1002/1099-0690(200106)2001:11<2055::aid-ejoc2055>3.0.co;2-n
Subject(s) - chemistry , trisaccharide , tetrasaccharide , glycosylation , intramolecular force , xylylene , stereochemistry , glycosyl donor , glycoside , yield (engineering) , glycosyl , protecting group , derivative (finance) , organic chemistry , polysaccharide , biochemistry , materials science , alkyl , economics , financial economics , metallurgy
Treatment of α,α′‐dibromo‐ m ‐xylylene with 6‐ O ‐unprotected thiomaltoside 4 as glycosyl donor (→ 5 ), followed by 4‐ O ‐unprotected galactoside derivative 6 as acceptor, afforded β‐linked macrocyclic trisaccharide 9β in high yield after removal of the 3‐ O ‐MPM protective group and subsequent intramolecular glycoside bond formation. Similarly, by the same sequence of steps, the corresponding tetrasaccharide 14β was obtained from 5 and 4b‐ O ‐unprotected lactoside 11 . For reiterative glycoside bond formation, treatment of α,α′‐dibromo‐ m ‐xylylene with 3‐ O ‐unprotected thioglycoside 15 as donor (→ 16 ), followed by 4,6‐ O ‐unprotected glucoside, and subsequent glycosylation afforded macrocyclic maltotrioside 22 , which was transformed into known maltotrioside 23 . A slight modification of the protecting‐group pattern in maltotrioside synthesis resulted in generally higher yields in the ligation of the building blocks to the m ‐xylylene spacer, particularly in the second glycosylation step, thus providing macrocyclic maltotrioside 40α , which was transformed into known maltotriosides 41α and 41β .