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

被引：1

作者：

Dabkowski, Wojciech ^{[1
]}

Helinski, Jan ^{[1
]}

Kazimierczak, Lucja ^{[1
]}

机构：

[1] Polish Acad Sci, Ctr Mol & Macromol Studies, Sienkiewicza 112, PL-90363 Lodz, Poland

来源：

ARKIVOC | 2010年

关键词：

Phosphitylation; thiono-thiolo (selenono-selenolo) rearrangement; fluorophosphoramidite; phosphoramidofluoridothioate (selenoate); MICHAELIS-ARBUZOV REARRANGEMENT; GLYCOSYL THIOPHOSPHATES; SELENOACIDS; PHOSPHORUS; THIOACIDS; BROMIDES;

D O I：

10.3998/ark.5550190.0011.a29

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 thiono- and selenono- esters 5 and 6. The latter compounds are readily rearranged into their thiolo- or selenolo- isomers in the presence of Bu4NI as catalyst (TBAI). The total yield of 7 and 8 exceeds 90%.

引用

页码：350 / 357

页数：8

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