Model synthesis of 2,3:5,6-di-O-isopropylidene- S-α-D-mannofuranosyl-N,N-diisopropylphosphoramidofluoridothioate and 2,3:5,6-di-O-isopropylidene-Se-α-D-mannofuranosyl-N,N-di-isopropylphosphoramidofluoridoselenoate via P(III)-OAr intermediates and a thiono-thiolo (selenono-selenolo) rearrangement

Content Provider	Semantic Scholar
Author	Dąbkowski, Wojciech Heliński, Jan Kazimierczak, Lucja
Copyright Year	2010
Abstract	Phosphitylation of the glycosidic center of sugar derivative 2 by phosphoroamidite 1 leads to the intermediate P(III) ester 3. Conversion of 3 into fluorophosphoroamidite 4 and subsequently oxidation by elemental sulfur or selenium affords the corresponding thionoand selenonoesters 5 and 6. The latter compounds are readily rearranged into their thioloor selenoloisomers in the presence of Bu4NI as catalyst (TBAI). The total yield of 7 and 8 exceeds 90%.
File Format	PDF HTM / HTML
DOI	10.3998/ark.5550190.0011.a29
Volume Number	2010
Alternate Webpage(s)	https://www.arkat-usa.org/get-file/35870/
Alternate Webpage(s)	http://www.arkat-usa.org/get-file/35870/
Alternate Webpage(s)	https://quod.lib.umich.edu/cgi/p/pod/dod-idx/model-synthesis-of-2356-di-o-isopropylidene-s-%CE%B1-d.pdf?c=ark&format=pdf&idno=5550190.0011.a29
Alternate Webpage(s)	https://doi.org/10.3998/ark.5550190.0011.a29
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article