کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1390129 | 1500842 | 2015 | 6 صفحه PDF | دانلود رایگان |
• Carbohydrate-based synthesis of a derivative of the amino sugar lemonose.
• Key sequence involves deoxygenation of a thiocarbonylimidazole derivative.
• Synthesis of novel thioglycoside and analysis by 2D-NMR and X-ray crystallography.
Lemonose is a component of the antibiotic lemonomycin and other antibiotics and natural products. Three routes to the synthesis of the title compound, a protected, desmethyl derivative of lemonose, from l-rhamnose or its glycal, were investigated based on electrophilic cyclization, epoxidation-ring opening, and deoxygenation of an intermediate that was used in the synthesis of the amino sugar callipeltose. The deoxygenation route was successful and it provided the title compound, which was then converted to a phenyl thioglycoside.
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Journal: Carbohydrate Research - Volume 409, 29 May 2015, Pages 63–68