期刊
TETRAHEDRON
卷 66, 期 9, 页码 1742-1759出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.12.031
关键词
-
资金
- Japan Society for the Promotion of Science [17GS0420]
- Grants-in-Aid for Scientific Research [17GS0420] Funding Source: KAKEN
A novel synthesis of tetralactosaminyl O-glycoamino acid is described The stereoselective assemblage of a lactosaminyl unit was performed by 2-trichloroacetamido group-assisted beta-glycosylation. Initial investigation into the synthesis of decasaccharyl threonine 2 showed limited Success because of the low yield in the step concerning the removal of 4-O-chloroacetyl groups In contrast, 4-O-benzylated decasaccharyl threonine 50 was efficiently synthesized from key LacNAc derivative 35 carrying a 3-O-allyl protecting group at the Gal residue by reiterative glycosylation using the (N-phenyl)trifluoroacetimidate method Decasaccharide 50 was used as a building block in the solid-phase synthesis of a MUC1-related glycopeptide Synthetic glycopeptide was obtained through two acidic processes cleavage from resin with reagent K at a lowered temperature and debenzylation with a diluted cocktail of low-acidity TfOH Desired glycopeptide 54 was isolated as the major product, while a series of the saccharide-shortened minor products were generated due to the acid-labile property of the beta-GlcNAc glycosidic linkages (C) 2009 Elsevier Ltd All rights reserved
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