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Volumn 51, Issue 43, 2010, Pages 5713-5717

A novel strategy toward the synthesis of N-(β-glycosyl)asparagines based on the alkylation of ethyl nitroacetate using N-(β-glycosyl) iodoacetamides

Author keywords

Alkylation; Chiral organocatalyst; Diastereoselectivity; Ethyl nitroacetate; Glycosylasparagine; N ( Glycosyl) iodoacetamides; N Glycoproteins

Indexed keywords

ACETAMIDE DERIVATIVE; ACETIC ACID DERIVATIVE; ANTHRACENE DERIVATIVE; ASPARAGINE DERIVATIVE; ETHYLNITROACETIC ACID; N (9 ANTHRACENYLMETHYL)CINCHONINIUM CHLORIDE; N (BETA GLYCOSYL)ASPARAGINE DERIVATIVE; N (BETA GLYCOSYL)IODOACETAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 77957162130     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.08.072     Document Type: Article
Times cited : (2)

References (39)
  • 31
    • 77957124333 scopus 로고    scopus 로고
    • note
    • 3 (207 mg, 1.5 mmol) in dry DMF (5 mL), ethyl nitroacetate (138 mg, 1 mmol) was added slowly at room temperature under nitrogen atmosphere. After stirring the reaction mixture for about 0.5 h, a solution of fully acetylated N-(β-d-glucopyranosyl) iodoacetamide (515 mg, 1 mmol) in dry DMF (3 mL) was added and stirring continued. The progress of the reaction was monitored by TLC analysis. Following completion of reaction in 6 h, the reaction mixture was diluted with ethyl acetate (50 mL). The resulting solution was washed with water (30 mL × 2), then with brine solution (30 mL), dried over anhydrous sodium sulfate and concentrated to dryness to get a sirup that was purified by column chromatography over silica gel (100-200 mesh) to obtain the product (7) as a mixture (55:45) of diastereomers.
  • 35
    • 77957150055 scopus 로고    scopus 로고
    • 13 The crude product obtained was purified by column chromatography (100-200 mesh) to furnish analytically pure products, 7-12, as diastereomeric mixtures
    • 13 The crude product obtained was purified by column chromatography (100-200 mesh) to furnish analytically pure products, 7-12, as diastereomeric mixtures.
  • 36
    • 77957131294 scopus 로고    scopus 로고
    • note
    • +. Found 542.1598.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.