2,3,4,6-Tetra-O-benzoyl-a-D-galactopyranosyl trichloroacetimidate - CAS 138479-78-4
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D-Galactose tetrabenzoate
1.Synthesis of the O-linked hexasaccharide containing β-D-Galp-(1→2)-D-Galf in Trypanosoma cruzi mucins. Differences on sialylation by trans-sialidase of the two constituent hexasaccharides.
Agustí R1, Giorgi ME1, Mendoza VM1, Kashiwagi GA1, de Lederkremer RM2, Gallo-Rodriguez C3. Bioorg Med Chem. 2015 Mar 15;23(6):1213-22. doi: 10.1016/j.bmc.2015.01.056. Epub 2015 Feb 7.
The hexasaccharide β-D-Galp-(1→2)-[β-D-Galp-(1→3)]-β-D-Galp-(1→6)-[β-D-Galp(1→2)-β-D-Galf(1→4)]-D-GlcNAc (10) and its β-D-Galf-(1→2)-β-D-Galf containing isomer (7) are the largest carbohydrates in mucins of some strains of Trypanosoma cruzi. The terminal β-D-Galp units are sites of sialylation by the parasite trans-sialidase. Hexasaccharide 10 was chemically synthesized for the first time by a [3+3] nitrilium based convergent approach, using the trichloroacetimidate method of glycosylation. The (1)H NMR spectrum of its alditol was identical to the spectrum of the product released by β-elimination from the parasite mucin. The trans-sialylation reaction studied on the benzyl glycoside of 10 showed two monosialylated products whose relative abundance changed with time. On the other hand, only one product was produced by sialylation of the benzyl glycoside of 7. A preparative synthesis of the latter and spectroscopic analysis of the product unequivocally established the sialylation site at the less hindered (1→3)-linked galactopyranose.
2.N-Bromoacetamide-mediated domino cyclization and elimination of homoallylic trichloroacetimidates: a novel approach toward the synthesis of 1-bromo-2-amino-3-butene derivatives.
Zhu R1, Yu K, Gu Z. Org Biomol Chem. 2014 Sep 14;12(34):6653-60. doi: 10.1039/c4ob01126k.
A practical synthesis of 1-bromo-2-amino-3-butene derivatives from homoallylic trichloroacetimidates was reported. Simply heating the mixture of substrates and N-bromoacetamide in DMF at 90 °C would give the desired products in moderate to excellent yields. The reaction may proceed through a domino bromo-cyclization and elimination pathway. The synthesis of 4,5-dihydrooxazoles from 1-bromo-2-amino-3-butene derivatives was also investigated.
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CAS 138479-78-4 2,3,4,6-Tetra-O-benzoyl-a-D-galactopyranosyl trichloroacetimidate

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