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. 2016 Jul 22:430:8-15.
doi: 10.1016/j.carres.2016.03.025. Epub 2016 Apr 6.

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

Shu-Lun Tang  1 , Nicola L B Pohl  2
Affiliations

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

Shu-Lun Tang et al. Carbohydr Res. .

Abstract

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 use of a C-5 ester as a protecting group that could be converted under reductive conditions to a hydroxymethyl group for chain extension.

Keywords: Automated oligosaccharide synthesis; Fluorous-assisted synthesis; β-Mannan; β-Mannuronate.

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Figures

Scheme 1
Scheme 1
Synthesis of building block 6 for the automated solution–phase synthesis of β-1,2-mannan.
Scheme 2
Scheme 2
Automated solution–phase synthesis of β-1,2-mannan 10.
Scheme 3
Scheme 3
Automated solution–phase synthesis of β-1,3-mannan 15.
Scheme 4
Scheme 4
Synthesis of the trichloroacetimidate building block 17 and automated solution-phase synthesis of β-1,6-mannan 20.
See this image and copyright information in PMC

References

    1. Schmaltz RM, Hanson SR, Wong CH. Chem Rev. 2011;111:4259–4307. - PubMed
    2. Crich D, Banerjee A, Yao Q. J Am Chem Soc. 2004;126:14930–14934. - PubMed
    3. Wu X, Bundle DR. J Org Chem. 2005;70:7381–7388. - PubMed
    4. Walters KR, Jr, Serianni AS, Sformo T, Barnes BM, Duman JG. Proc Natl Acad Sci, USA. 2009;106:20210–20215. - PMC - PubMed
    5. Ishiwata A, Sakurai A, Nishimiya Y, Tsuda S, Ito Y. J Am Chem Soc. 2011;133:19524–19535. - PubMed
    6. Crich D, Rahaman MY. J Org Chem. 2011;76:8611–8620. - PMC - PubMed
    1. Iwamoto M, Kurachi M, Nakashima T, Kim D, Yamaguchi K, Oda T, Iwamoto Y, Muramatsu T. FEBS lett. 2005;579:4423–4429. - PubMed
    2. Janeway CA, Jr, Medzhitov R. Annu Rev Immunol. 2002;20:197–216. - PubMed
    1. Heuckendorff M, Bendix J, Pedersen CM, Bols M. Org Lett. 2014;16:1116–1119. - PubMed
    2. Baek JY, Lee BY, Jo MG, Kim KS. J Am Chem Soc. 2009;131:17705–17713. - PubMed
    3. Stork G, La Clair JJ. J Am Chem Soc. 1996;118:247–248.
    4. Wu X, Bundle DR. J Org Chem. 2005;70:7381–7388. - PubMed
    1. Codee JDC, Kroeck L, Castagner B, Seeberger PH. Chem—Eur J. 2008;14:3987–3994. - PubMed
    2. Walvoort MTC, van den Elst H, Plante OJ, Kröck L, Seeberger PH, Overkleeft HS, van der Marel GA, Codée JDC. Angew Chem Int Ed. 2012;51:4393–4396. - PubMed
    3. Dallabernardina P, Schuhmacher F, Seeberger PH, Pfrengle F. Org Biomol Chem. 2016;14:309–313. - PubMed
    1. Pohl NL. ACS Symp Ser. 2008;990:272–287.
    2. Tang SL, Pohl NLB. Org Lett. 2015;17:2642–2645. - PMC - PubMed
    3. Tang SL, Linz LB, Bonning BC, Pohl NLB. J Org Chem. 2015;80:10482–10489. - PMC - PubMed