Significant solvent effect in anomerization reaction of pyranosides with 2,3-trans carbamate and carbonate

Tetrahedron Letters

Volumn 50, Issue 34, 2009, Pages 4827-4829

  Manabe, Shino ^a   Ito, Yukishige ^a  

^a RIKEN   (Japan)

Author keywords

Anomerization; Endocyclic cleavage; Pyranosides; Solvent effect

Indexed keywords

2,3 TRANS CARBAMATE; CARBAMIC ACID DERIVATIVE; CARBONIC ACID; PYRANOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SOLVENT EFFECT; SYNTHESIS; TEMPERATURE MEASUREMENT;

EID: 67649886235     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.05.119     Document Type: Article

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33. 3 was added. The aqueous layer was extracted with EtOAc. The combined layers were washed with brine. After drying the organic layers, the solvent was evaporated. The residue was purified by preparative TLC (hexane/EtOAc 7:3). The β-thioglycoside 1 (7.8 mg, 10%) and α-thioglycoside 2 (69.0 mg, 89%) were obtained.