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Volumn 16, Issue 22, 2006, Pages 5736-5739

Odorless benzenethiols in synthesis of thioglycosides and its application for glycosylation reactions

Author keywords

Glycosylation; Odorless thiols; p Octyloxybenzenethiol; Thioglycosides

Indexed keywords

4 OCTYLOXYBENZENETHIOL; GLYCOSIDE; N IODOSUCCINIMIDE; SILVER DERIVATIVE; SILVER TRIFLATE; SUCCINIMIDE DERIVATIVE; THIOGLYCOSIDE; THIOPHENOL DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

EID: 33749460458     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.08.095     Document Type: Article
Times cited : (27)

References (28)
  • 17
    • 33749498097 scopus 로고    scopus 로고
    • note
    • 4 (600 mg) in refluxed tetrahydrofuran (45 ml) for 10 h. The reaction residue obtained by usual work-up was purified by silica gel column chromatography (hexane/ethyl acetate = 100:1) afforded 2.
  • 18
    • 33749501535 scopus 로고    scopus 로고
    • note
    • 2), 4.19 (dd, A part of AB type, J = 2.4 and 12.3 Hz, 1H, H-6), 4.27 (dd, B part of AB type, J = 4.6 and 12.3 Hz, 1H, H-6), 4.28 (t, J = 10.1 Hz, H-4, 1H), 5.09 (t, J = 9.6 Hz, 1H, H-3), 5.57 (d, J = 10.5 Hz, 1H, H-1), 5.75 (dd, J = 10.5 and 9.6 Hz, H-2), 6.78 and 7.33 (each d, AB type, J = 8.8 Hz, 1H), 7.75 and 7.88 (each dd, AB type, J = 3.0 and 5.3 Hz, 1H).
  • 19
    • 33749501282 scopus 로고    scopus 로고
    • note
    • 4, and condensed in vacuo. The residue was purified by silica gel chromatography to afford the desired thioglycoside.
  • 22
    • 33749483259 scopus 로고    scopus 로고
    • note
    • 2), 4.01 (dd, J = 3.5 and 9.9 Hz, 1H), 4.12 (t, J = 9.9 Hz, 1H), 4.23 (dd, J = 4.8 and 10.3 Hz, 1H), 4.38 (dt, J = 4.8 and 9.9 Hz, 1H), 4.68 and 4.73 (each d, AB type, J = 12.2 Hz, 1H), 5.28 (d, J = 1.5 Hz, 1H, H-1), 5.60 (dd, J = 1.5 and 3.5 Hz, 1H, H-2), 5.64 (s, 1H, PhCH<), 6.81 (d, J = 8.8 Hz, 2H), 7.2-7.4 (m, 10H), 7.52 (d, J = 8.8 Hz, 2H).
  • 24
    • 33749485818 scopus 로고    scopus 로고
    • note
    • 3); δ: 0.1 (s, 9H), 1.0 (m, 2H), 2.16 (s, 3H), 3.4-4.1 (m, 13H), 4.20 (br d, J = 6.0 Hz, 1H), 4.37 (d, J = 7.9 Hz, 1H), 4.50 (d, J = 11.0 Hz, 1H), 4.63 (d, J = 11.9 Hz, A part of AB, 1H), 4.70 (d, J = 11.9 Hz, B part of AB, 1H), 4.74 (dd, J = 4.0 and 11.0 Hz, 1H), 4.81 (d, J = 10.0 Hz, 1H), 4.86 (d, J = 1.5 Hz, 1H, man-1), 4.96 (dd, J = 4.3 and 11.0 Hz, 2H), 5.46 (dd, J = 1.5 and 4.0 Hz, 1H, man-2), 5.61 (s, 1H, PhCH<), 7.1-7.4 (m, 23H), 7.46 (m, 2H).
  • 25
    • 33749471706 scopus 로고    scopus 로고
    • note
    • 4, and condensed in vacuo. The residue was purified by silica gel chromatography.
  • 26
    • 33749494454 scopus 로고    scopus 로고
    • note
    • 3); δ: -0.01 (s, 9H), 1.05 (m, 2H), 1.83 (s, 3H, NHAc), 2.01, 2.02, and 2.03 (each s, 3H, OAc), 3.76 and 3.44 (each t, J = 9.0 Hz, 2H), 3.55-3.95 (m, 12H), 4.05-4.25 (m, 5H), 4.27 (dd, J = 5.0 and 12.1 Hz, 1H), 4.40 (d, J = 10.4 Hz, 1H), 4.42 (d, J = 13.4 Hz, 1H), 4.73 (s, 2H), 4.75-4.80 (m, 2H), 4.84 (d, J = 1.7 Hz, 1H), 4.90-5.05 (m, 2H), 5.04 (d, J = 19.8 Hz, 1H), 5.52 (dd, J = 1.7 and 3.0 Hz, 1H, man-2), 5.53 (d, J = 19.8 Hz, 1H), 5.59 (s, 1H, PhCH<), 7.1-7.4 (m, 23H), 7.43 (m, 2H).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.