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- W2113440167 abstract "New 2/1-type surfactants were synthesized from glycerol derivatives 2a–e having a long-chain 2-O-alkyl substituent. Transformation of 2a–d into 1,3-di-O-trifluoromethanesulfonates 4a–d and their use in anomeric O-alkylation of mannofuranose 7 afforded after protective group removal β-linked bis-mannofuranosides 13a–d. Preparation of mono-O-benzyl-protected compounds 5b–e from 2b–e, trifluoromethyanesulfonate formation, and then anomeric O-alkylation of 7 gave after O-debenzylation 1-O-mannofuranosides 10b–e. Their unprotected 3-hydroxy group was employed for the attachment of a β-glucopyranosyl residue (→ 15b–e) and a sulfate group (→ 18b–e). Transformation of 10b–e into alkylating agents 19b–e and 20b–e, respectively, enabled the attachment of the malonate group (→ 17b–e), oligoethylene glycol residues (→ 28b–e, 29b–e, 30b–e), iminodiacetic acid (→ 32b–e), and of the aspartate residue (→ 34b–e) as second hydrophilic group. Surface tension (σs) and critical micelle concentration (cmc) measurements with these compounds are reported and the results discussed." @default.
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- W2113440167 date "2006-01-25" @default.
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- W2113440167 title "Anomeric O-Alkylation, 15. New 2/1-Type Surfactants by Anomeric O-Alkylation of Mannofuranose" @default.
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- W2113440167 doi "https://doi.org/10.1002/jlac.199619960811" @default.
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