Reference of 14215-68-0, An article , which mentions 14215-68-0, molecular formula is C8H15NO6. The compound – N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide played an important role in people’s production and life.
Glycosylidene Carbenes Part 4 Synthesis of Spirocyclopropanes from Acetamidoglycosylidene-Derived Diazirines
The synthesis of the first glycosylidene-derived 2-acetamido-2-deoxydiazirine 4 from N-acetylglucosamine 6 is described.Thus, 6 was transformed into the 3-O-mesylglucopyranoside 9 by glycosidation with allyl alcohol, benzylidenation, and mesylation (Scheme 2).Solvolysis of 9 gave the allopyranoside 10 which, upon benzylation and glycoside cleavage, yielded the hemiacetals 12.Using our established method (via the lacton oxime 14 and the diaziridines 16), 12 gave the diazirine 4.Thermolysis of this diazirine in the presence of i-PrOH gave the dihydro-1,3-oxazole 5 (Scheme 1); in the presence of acrylonitrile, the four diastereomeric spirocyclopropanes 17-20 and the acetamidoallal 21 were obtained and separated by prep.HPLC (Scheme 3).Assignment of the configuration of 17-20 is based on NOE measurements and on the effect of diamagnetic anisotropy of the CN group.The ratio of the four cyclopropanes, which is in keeping with earlier results, is rationalized.
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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics