Electric Literature of 10034-20-5. Let’s face it, organic chemistry can seem difficult to learn. Especially from a beginner’s point of view. Like 10034-20-5, Name is (2S,3R,4R,5S,6R)-6-(Acetoxymethyl)-3-aminotetrahydro-2H-pyran-2,4,5-triyl triacetate hydrochloride. In a document type is Article, introducing its new discovery.
The use of 2-deoxy-2-trichloroacetamido-D-glucopyranose derivatives in syntheses of oligosaccharides
3,4,6-Tri-O-acetyl-2-deoxy-2-trichloroacetamido-alpha-D-glucopyranosyl trichloroacetimidate and its O-benzylated analogue were tested as glycosyl donors in the reaction with a set of sugar acceptors unsubstituted on O-3 and O-4, typically encountered in the synthesis of oligosaccharides.Glycosides were obtained in good to excellent yields with only a slight excess (1.1-1.2 equiv) of the donor, and with a high degree of 1,2-trans stereoselectivity.The corresponding 2-(trichloromethyl)oxazolinium ion was postulated to be the major reactive intermediate.The N-trichloroacetyl groups in the disaccharide products were easily transformed into N-acetyl under neutral conditions by reduction with tributylstannane.
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Reference：
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics