A Convenient Route to Peracetylated 3-Deoxy-3-fluoro Analogues of D-Glucosamine

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F67985858%3A_____%2F14%3A00428290" target="_blank" >RIV/67985858:_____/14:00428290 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1055/s-0033-1341187" target="_blank" >http://dx.doi.org/10.1055/s-0033-1341187</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1055/s-0033-1341187" target="_blank" >10.1055/s-0033-1341187</a>

Result language
angličtina
Original language name
A Convenient Route to Peracetylated 3-Deoxy-3-fluoro Analogues of D-Glucosamine
Original language description
Peracetylated 3-deoxy-3-fluoro analogues of D-glucosamine and D-galactosamine 3 and 4, respectively, were prepared from 1,6:2,3-dianhydro-4-O-benzyl-?-D-mannopyranose (6). Azidolysis of 6 followed by reaction with diethylaminosulfur trifluoride gave 1,6-anhydro-2-azido-4-O-benzyl-2,3-dideoxy-3-fluoro- ?-D-glucopyranose (9). Cleavage of the internal acetal, hydrogenation and acetylation yielded 3. De-O-benzylation of 9 followed by a configurational inversion at C4 gave 1,6-anhydro-2-azido-2,3-dideoxy- 3-fluoro-?-D-galactopyranose (18), which provided 4 after cleavage of the 1,6-anhydro bridge, reduction, and acetylation.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2014
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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