Abstract
The branched, sulfur-linked tetrasaccharide S-(beta-D-glucopyranosyl)-(1-->3)-S-[(6-S-beta-D-glucopyranosyl)-3,6-dit hio- beta-D-glucopyranosyl]-(1-->3)-S-3-thio-D-glucopyranose (9) has been conveniently prepared by SN2 displacement of the triflate group in 1,2:5,6-di-O-isopropylidene-3-O-trifluoromethylsulfonyl-alpha-D-++ +allofuranose with the sodium salt of 2,4-di-O-acetyl-3,6-di-S-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)- 1,3,6- trithio-beta-D-glucopyranose (5). Conversely, reaction of the sodium salt of 5 with 1,2,3,4-tetra-O-acetyl-6-deoxy-6-iodo-beta-D-glucopyranose afforded the positional isomer S-(beta-D-glucopyranosyl)-(1-->6)-S-[(3-S-beta-D-glucopyranosyl)-3,6-dit hio- beta-D-glucopyranosyl]-(1-->6)-S-6-thio-D-glucopyranose (12).
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Adjuvants, Immunologic / chemical synthesis
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Adjuvants, Immunologic / pharmacology
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Antineoplastic Agents, Phytogenic / chemical synthesis
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Antineoplastic Agents, Phytogenic / pharmacology
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Carbohydrate Conformation
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Carbohydrate Sequence
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Fungi / chemistry
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Magnetic Resonance Spectroscopy
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Molecular Sequence Data
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Molecular Structure
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Oligosaccharides / chemical synthesis
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Repetitive Sequences, Nucleic Acid
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Sizofiran / analogs & derivatives*
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Sizofiran / chemical synthesis
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Thioglucosides / chemical synthesis*
Substances
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Adjuvants, Immunologic
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Antineoplastic Agents, Phytogenic
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Oligosaccharides
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S-(glucopyranosyl)(1-3)-S-((6-S-glucopyranosyl)-3,6-dithioglucopyranosyl)(1-3)-S-3-thioglucopyranose
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Thioglucosides
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Sizofiran