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.
2,3,4,6-tetra-O-Acetyl-D-gluconic acid was synthesized and coupled with 1,3,4, 6-tetra-O-acetyl-2-amino-2-deoxy-beta-D-glucopyranose and diosgenyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-beta-D-glucopyranoside to afford N-gluconyl derivatives of diosgenyl 2-amino-2-deoxy-D-glucopyranoside using the methods of solution-phase peptide synthesis. Both coupling reactions suffered from acetyl O?N migration, which caused the N-acetyl derivatives to be formed together with the N-(D-gluconyl) derivatives of D-glucosamine. Additionally, single-crystal X-ray diffraction and high-resolution NMR spectral data for 2,3,4,6-tetra-O-acetyl-D-gluconic acid were analyzed to reveal that this acyclic carbohydrate has adopted the 2G- conformation instead of a typical zigzag conformation. The planarity and cis geometry of the acetoxyl groups are demonstrated.
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Reference£º
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics