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Volumn , Issue 18, 2007, Pages 2837-2840

Bisglycosyl peroxides

Author keywords

2 deoxysugars; Addition reactions; Glycals; Glycosylations; Peroxides

Indexed keywords

PEROXIDE;

EID: 36649026924     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-991090     Document Type: Article
Times cited : (5)

References (36)
  • 2
    • 32444447135 scopus 로고    scopus 로고
    • Corrigendum: Kośnik, W.; Stachulski, A.; Chmielewski, M. Tetrahedron: Asymmetry 2006, 17, 313.
    • (b) Corrigendum: Kośnik, W.; Stachulski, A.; Chmielewski, M. Tetrahedron: Asymmetry 2006, 17, 313.
  • 11
    • 36649035290 scopus 로고    scopus 로고
    • Formation of Bisglycosyl Peroxides; General Procedure: To a stirred solution of hydroperoxides 1, 2, 3, 5 or 7 (0.11 mmol) and tri-O-benzyl-D-glucal or tri-O-benzyl-D- galactal (0.12 mmol) in anhyd CH2Cl2 (5 mL) was added (1S, )-10-camphorsulfonic acid (0.08 mmol, The reaction was stirred overnight (glucal) or 2 h (galactal) and quenched with NaHCO3, then filtered and concentrated to dryness. Column chromatography of the residue with hexane-EtOAc (75:25) gave the respective products. Bis-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl Peroxide (9, oil; yield: 44.6, α]D +136 (c, 0.64, CH2Cl 2, IR (film, 1104, 736, 697 cm-1. 1H NMR (500 MHz, CDCl3):18 δ, 5.46 (d, J, 3.4 Hz, 1 H, H-1, 4.42-4.85 (m, 6 H, 3 x Bn, 3.95 ddd, J, 2.1, 3.2, 9.9 H
    • 18 δ = 99.97, 99.60 (C-1′, C-1), 77.91, 77.10, 74.88 (Bn), 74.45 (Bn), 74.18, 73.46 (Bn), 73.40 (Bn), 72.70, 71.89 (Bn), 71.50, 70.48, 70.47 (Bn), 68.89, 68.68 (C-6′, C-6), 33.12, 28.84 (C-2, C-2′). HRMS (ESI).
  • 36
    • 36649033109 scopus 로고    scopus 로고
    • 13C NMR resonances for phenyl groups are not reported.
    • 13C NMR resonances for phenyl groups are not reported.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.