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One-pot protection-glycosylation reactions for synthesis of lipid?II analogues.

ABSTRACT: (2,6-Dichloro-4-methoxyphenyl)(2,4-dichlorophenyl)methyl trichloroacetimidate (3) and its polymer-supported reagent 4 can be successfully applied to a one-pot protection-glycosylation reaction to form the disaccharide derivative 7?d for the synthesis of lipid?II analogues. The temporary protecting group or linker at the C-6 position and N-Troc protecting group of 7?d can be cleaved simultaneously through a reductive condition. Overall yields of syntheses of lipid?II (1) and neryl-lipid?II N(?)-dansylthiourea are significantly improved by using the described methods.

SUBMITTER: Mitachi K

PROVIDER: S-EPMC4030666 | biostudies-literature | 2014 Apr

REPOSITORIES: biostudies-literature

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One-pot protection-glycosylation reactions for synthesis of lipid II analogues.

Mitachi Katsuhiko K Mohan Priya P Siricilla Shajila S Kurosu Michio M

Chemistry (Weinheim an der Bergstrasse, Germany) 20140312 16

(2,6-Dichloro-4-methoxyphenyl)(2,4-dichlorophenyl)methyl trichloroacetimidate (3) and its polymer-supported reagent 4 can be successfully applied to a one-pot protection-glycosylation reaction to form the disaccharide derivative 7 d for the synthesis of lipid II analogues. The temporary protecting group or linker at the C-6 position and N-Troc protecting group of 7 d can be cleaved simultaneously through a reductive condition. Overall yields of syntheses of lipid II (1) and neryl-lipid II N(ε)-d ...[more]

PMID: 24623584

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