Synthesis of C-Oligosaccharides That Mimic Their Natural O-Analogous Immunodeterminants in Binding to Monoclonal Immunoglobulins

Abstract

We have stereoselectively synthesized the analogues of the methyl β‐glycosides of (1→6)‐β‐D‐galacto‐oligosaccharides (up to tetrasaccharide), in which the interglycosidic oxygen atoms are replaced by a methylene group.

Recent Advances in the Synthesis of C‐Oligosaccharides

“…The lactone-addition methodology was later applied by Sinaÿ and co-workers in an iterative fashion for the preparation of higher homologues [33]. Hydroxylmethylene in compound 141 was converted to acetylide lithium in compound 142 by a sequence of reactions.…”

Recent Advances in the Synthesis of C‐Oligosaccharides

“…The lactone-addition methodology was later applied by Sinaÿ and co-workers in an iterative fashion for the preparation of higher homologues [33]. Hydroxylmethylene in compound 141 was converted to acetylide lithium in compound 142 by a sequence of reactions.…”

Formation of the Glycosidic Linkage

“…Of general usage is the method developed by Kishi, the addition of an organometallic reagent to an aldonolactone: 424,425 Epoxides and glycals are useful alkylating agents of nucleophilic species: 424,[426][427][428] Hemiacetals, upon chain extension with phosphoranes, phosphonates or organometallic species, yield alkenes that cyclize either spontaneously or by treatment with bases or electrophiles:…”

Recent Advances in the Synthesis of C‐Oligosaccharides

“…The lactone-addition methodology was later applied by Sinaÿ and co-workers in an iterative fashion for the preparation of higher homologues [33]. Hydroxylmethylene in compound 141 was converted to acetylide lithium in compound 142 by a sequence of reactions.…”

Formation of the Glycosidic Linkage

“…Of general usage is the method developed by Kishi, the addition of an organometallic reagent to an aldonolactone: 424,425 Epoxides and glycals are useful alkylating agents of nucleophilic species: 424,[426][427][428] Hemiacetals, upon chain extension with phosphoranes, phosphonates or organometallic species, yield alkenes that cyclize either spontaneously or by treatment with bases or electrophiles:…”

Recent Advances in the Synthesis of C‐Oligosaccharides

“…The lactone-addition methodology was later applied by Sinaÿ and co-workers in an iterative fashion for the preparation of higher homologues [33]. Hydroxylmethylene in compound 141 was converted to acetylide lithium in compound 142 by a sequence of reactions.…”

Formation of the Glycosidic Linkage

“…Of general usage is the method developed by Kishi, the addition of an organometallic reagent to an aldonolactone: 424,425 Epoxides and glycals are useful alkylating agents of nucleophilic species: 424,[426][427][428] Hemiacetals, upon chain extension with phosphoranes, phosphonates or organometallic species, yield alkenes that cyclize either spontaneously or by treatment with bases or electrophiles:…”