Synthesis of a precursor of β-d-glcpnac(l-→2)-α-d-manp-(l-→-3)-[β-d-xylp-(1 →2)]-β-d-manp-(1→4) - β-d-glcp1

Osamu Kanie, Tadahiro Takeda, Noriyasu Hada, Yukio Ogihara

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

The glycosphingolipids isolated from spermatozoa of a fresh-water bivalve, Hyriopsis schlegelii, have a unique structure containing one or two mannosyl residues, novel linkages including an internal fucopyranosyl residue, as well as terminal xylosyl and 4-0-methyl-D-glucopyranosyl uronic acid groups. The pentasaccharide derivatives that constitute the partial structure of lipid IV were synthesized as follows. 4, 6-Di-0.-acetyl-2-0-(2, 3, 4 -tri-0-acetyl-β-D-xylopyran-osyl)-3-0benzyl-a-D-mannopyranosyl bromide was treated with 2, 3-di-0-acetyl-1, 6-anhydro-p-D-glucopyranose in the presence of silver zeolite to afford the corresponding trisaccharide. The formation of the p-glycoside took precedence as a major product in a ratio of 6.9:1. After debenzylation, the p-mannosyl trisaccharide derivative was condensed with 3, 4, 6-tri-0-acetyl-2-0.-chloroacetyl- a -D-mannopyranosyl bromide in the presence of silver triflate, and the final pentasaccharide derivative was prepared by using a suitably protected tetrasaccharide as the glycosyl acceptor, 3-0-acetyl-6-07benzyl-4-()-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide as the donor and silver triflate as the promoter, respectively.

Original languageEnglish
Pages (from-to)561-581
Number of pages21
JournalJournal of Carbohydrate Chemistry
Volume10
Issue number4
DOIs
Publication statusPublished - 1991 Jan 1
Externally publishedYes

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Bromides
Trisaccharides
Derivatives
Uronic Acids
Zeolites
Glycosphingolipids
Bivalvia
Glycosides
Fresh Water
Silver
Spermatozoa
Water
trifluoromethanesulfonic acid

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

Cite this

Synthesis of a precursor of β-d-glcpnac(l-→2)-α-d-manp-(l-→-3)-[β-d-xylp-(1 →2)]-β-d-manp-(1→4) - β-d-glcp1. / Kanie, Osamu; Takeda, Tadahiro; Hada, Noriyasu; Ogihara, Yukio.

In: Journal of Carbohydrate Chemistry, Vol. 10, No. 4, 01.01.1991, p. 561-581.

Research output: Contribution to journalArticle

Kanie, Osamu ; Takeda, Tadahiro ; Hada, Noriyasu ; Ogihara, Yukio. / Synthesis of a precursor of β-d-glcpnac(l-→2)-α-d-manp-(l-→-3)-[β-d-xylp-(1 →2)]-β-d-manp-(1→4) - β-d-glcp1. In: Journal of Carbohydrate Chemistry. 1991 ; Vol. 10, No. 4. pp. 561-581.
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abstract = "The glycosphingolipids isolated from spermatozoa of a fresh-water bivalve, Hyriopsis schlegelii, have a unique structure containing one or two mannosyl residues, novel linkages including an internal fucopyranosyl residue, as well as terminal xylosyl and 4-0-methyl-D-glucopyranosyl uronic acid groups. The pentasaccharide derivatives that constitute the partial structure of lipid IV were synthesized as follows. 4, 6-Di-0.-acetyl-2-0-(2, 3, 4 -tri-0-acetyl-β-D-xylopyran-osyl)-3-0benzyl-a-D-mannopyranosyl bromide was treated with 2, 3-di-0-acetyl-1, 6-anhydro-p-D-glucopyranose in the presence of silver zeolite to afford the corresponding trisaccharide. The formation of the p-glycoside took precedence as a major product in a ratio of 6.9:1. After debenzylation, the p-mannosyl trisaccharide derivative was condensed with 3, 4, 6-tri-0-acetyl-2-0.-chloroacetyl- a -D-mannopyranosyl bromide in the presence of silver triflate, and the final pentasaccharide derivative was prepared by using a suitably protected tetrasaccharide as the glycosyl acceptor, 3-0-acetyl-6-07benzyl-4-()-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide as the donor and silver triflate as the promoter, respectively.",
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