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Volumn 51, Issue 17, 1995, Pages 4923-4932

A stereoselective glycosidation using thioglycosides, activation by combination of N-bromosuccinimide and strong acid salts

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE;

EID: 0028962740     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)98690-J     Document Type: Article
Times cited : (78)

References (35)
  • 14
    • 84988126671 scopus 로고
    • Nitriles as Solvents in Glycosylation Reactions: Highly Selective β-Glycoside Synthesis1
    • (1990) Synlett , pp. 694
    • Schmidt1    Behrendt2    Toepfer3
  • 26
    • 0012806751 scopus 로고
    • Catalytic Stereoselective Synthesis of .ALPHA.- or ,.BETA.-Glucosides Using a Single Glycosyl Donor, 1-O-2'-(2'-Methoxyethoxy)acetyl-Glucopyranose Derivative.
    • (1993) Chemistry Letters , pp. 1373
    • Matsubara1    Sasaki2    Mukaiyama3
  • 29
    • 84916473814 scopus 로고    scopus 로고
    • 2g,4a,9a,10b-e,
  • 30
    • 84916466701 scopus 로고    scopus 로고
    • 4 (0.5 equiv.) also promoted glycosidation of 6 with thioglycoside 1 in ether effectively to give corresponding disaccharide 9 in 72% yield, though the selectivity was not satisfactory (α:β = 1 : 0.57).
  • 31
    • 84916493157 scopus 로고    scopus 로고
    • 18, These results will be published soon elsewhere.
  • 32
    • 84916465398 scopus 로고    scopus 로고
    • The corresponding glycosyl bromide was obtained quantitatively from thioglycoside 1 by the use of NBS and silica gel in the absence of glycosyl acceptor in ether at −20 °C for 40 min.
  • 33
    • 84916491445 scopus 로고    scopus 로고
    • 4.
  • 34
    • 84916507082 scopus 로고    scopus 로고
    • 4 (0.05 equiv.) and silica gel at −20 °C during 3 d to give disaccharide 9: Yield 18% (α:β=1:0.17). Therefore, the glycosidation with thioglycoside 1 using silica gel under the prolonged reaction conditions may proceed partly via the glycosyl bromide to give disaccharide 9 with lower α-selectivity.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.