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Automated fluorous-assisted solution-phase synthesis of ?-1,2-, 1,3-, and 1,6-mannan oligomers.

ABSTRACT: Automated solution-phase syntheses of ?-1,2-, 1,3-, and 1,6-mannan oligomers have been accomplished by applying a ?-directing C-5 carboxylate strategy. Fluorous-tag-assisted purification after each reaction cycle allowed the synthesis of short ?-mannan oligomers with limited loading of glycosyl donor-as low as 3.0 equivalents for each glycosylation cycle. This study showed the capability of the automated solution-phase synthesis protocol for synthesizing various challenging glycosides, including use of a C-5 ester as a protecting group that could be converted under reductive conditions to a hydroxymethyl group for chain extension.

SUBMITTER: Tang SL

PROVIDER: S-EPMC4893899 | biostudies-literature | 2016 Jul

REPOSITORIES: biostudies-literature

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Automated fluorous-assisted solution-phase synthesis of β-1,2-, 1,3-, and 1,6-mannan oligomers.

Tang Shu-Lun SL Pohl Nicola L B NLB

Carbohydrate research 20160406

Automated solution-phase syntheses of β-1,2-, 1,3-, and 1,6-mannan oligomers have been accomplished by applying a β-directing C-5 carboxylate strategy. Fluorous-tag-assisted purification after each reaction cycle allowed the synthesis of short β-mannan oligomers with limited loading of glycosyl donor-as low as 3.0 equivalents for each glycosylation cycle. This study showed the capability of the automated solution-phase synthesis protocol for synthesizing various challenging glycosides, including ...[more]

PMID: 27155895

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