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. 2019 Jan 18;84(2):516-525.
doi: 10.1021/acs.joc.8b01949. Epub 2019 Jan 2.

Regioselective Manipulation of GlcNAc Provides Allosamine, Lividosamine, and Related Compounds

Ji Zhang  1 , Niek N H M Eisink  1 , Martin D Witte  1 , Adriaan J Minnaard  1
Affiliations

Regioselective Manipulation of GlcNAc Provides Allosamine, Lividosamine, and Related Compounds

Ji Zhang et al. J Org Chem. .

Abstract

Palladium-catalyzed oxidation of isopropyl N-acetyl-α-d-glucosamine (GlcNAc) is used to prepare the rare sugars allosamine, lividosamine, and related compounds with unprecedented selectivity. The Passerini reaction applied on 3-keto-GlcNAc provides an entry into branching of the carbon skeleton in this compound.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Site-Selective Palladium-Catalyzed Oxidation of Unprotected Carbohydrates
Scheme 2
Scheme 2. Jeanloz Synthesis of d-Allosamine and d-N-Acetyl Allosamine
Scheme 3
Scheme 3. Synthesis of d-Allosamine and N-Acetyl-d-allosamine
Figure 1
Figure 1
X-ray structure of boc-hydrazone 24.
Scheme 4
Scheme 4. Synthesis of d-Lividosamine
Scheme 5
Scheme 5. Synthesis of 2,3-Di-amino Glucose and a Corresponding Fused Imidazole
Scheme 6
Scheme 6. Passerini Reaction with 1-Isopropyl-3-keto GlcNAc
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References

    1. Elshahawi S. I.; Shaaban K. A.; Kharel M. K.; Thorson J. S. A comprehensive review of glycosylated bacterial natural products. Chem. Soc. Rev. 2015, 44, 7591–7697. 10.1039/C4CS00426D. - DOI - PMC - PubMed
    1. Brimacombe S. J. The Synthesis of Rare Sugars. Angew. Chem., Int. Ed. Engl. 1969, 8, 401–409. 10.1002/anie.196904011. - DOI
    2. Skarbek K.; Milewska M. J. Biosynthetic and synthetic access to amino sugars. Carbohydr. Res. 2016, 434, 44–71. 10.1016/j.carres.2016.08.005. - DOI - PubMed
    1. Martínez R. F.; Liu Z.; Glawar A. F.; Yoshihara A.; Izumori K.; Fleet G. W. J.; Jenkinson S. F. Short and Sweet: d-Glucose to l-Glucose and l-Glucuronic Acid. Angew. Chem., Int. Ed. 2014, 53, 1160–1162. 10.1002/anie.201309073. - DOI - PubMed
    1. Lenagh-Snow G. M. J.; Araújo N.; Jenkinson S. F.; Martínez R. F.; Shimada Y.; Yu C.-Y.; Kato A.; Fleet G. W. J. Azetidine Iminosugars from the Cyclization of 3,5-Di-O-triflates of α-Furanosides and of 2,4-Di-O-triflates of β-Pyranosides Derived from Glucose. Org. Lett. 2012, 14, 2142–2145. 10.1021/ol300669v. - DOI - PubMed
    1. Lenagh-Snow G. M. J.; Jenkinson S. F.; Newberry S. J.; Kato A.; Nakagawa S.; Adachi I.; Wormald M. R.; Yoshihara A.; Morimoto K.; Akimitsu K.; Izumori K.; Fleet G. W. J. Eight Stereoisomers of Homonojirimycin from d-Mannose. Org. Lett. 2012, 14, 2050–2053. 10.1021/ol3005744. - DOI - PubMed

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