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Synthesis of acylated tri- and tetra-saccharides with one thioureylene group
Monosaccharides joined by urea or thiourea groups, non-ionic isoteric bridges of phosphates, have been studied. These bridges are present in a few natural products such as glycocinnamoylspermidines, a family of broad spectrum antibiotics. Jochims and Seeliger described the first thiourea derivative in which both nitrogen atoms are joined to non-anomeric carbon atoms. In this paper the authors describe the preparation of the ethyl 2-deoxy-2-isothiocyanato-gentiobiosides 1 and 2, the p- methylphenacylthiourea 3, and the thioureylene-trisaccharides (4 anmd 5) and tetrasaccharides (6 abd 7) in which the thourea group joins non-anomeric carbon atoms of mono- or di-saccharides.
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Reference：
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics