Sc(OTf)3 as Efficient Catalyst for Aryl C-Glycoside Synthesis

Synlett

Volumn , Issue 2, 2004, Pages 225-230

  Ben, Akimi ^a   Yamauchi, Takahito ^a   Matsumoto, Takashi ^a   Suzuki, Keisuke ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Aryl C glycosides; Catalysis; O C glycoside rearrangement; Ravidomycin; Scandium triflate

Indexed keywords

ACETIC ACID; AZIDE; GLYCOSIDE; LEWIS ACID; PHENOL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SUGAR;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CATALYSIS; CATALYST; CONCENTRATION RESPONSE; DRUG SYNTHESIS; GLYCOSYLATION; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR MECHANICS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 1242296151     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-44988     Document Type: Article

References (41)

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36. This work was presented at the 83rd Annual Meeting of the Chemical Society of Japan, March 2003, Tokyo, Abstract 2D-1-38.
37. The α-isomer was used for this study. Synthesis of 2 will be reported elsewhere.
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39. 13C NMR, NOE and HMBC are shown below (Figure 2). (Equation Presented) Figure 2
40. 4. Removal of the solvents in vacuo and purification by silica-gel column chromatography (hexane/EtOAc = 5:1) afforded C-glycoside β-4 as white powder (462 mg, 78%).
41. 4. Removal of the solvents in vacuo and purification on silica-gel preparative TLC (hexane/acetone = 2:1) afforded C-glycoside 6a as white powder (75.9 mg, 89%).