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Synlett
Volumn , Issue 17, 2007, Pages 2738-2742
Spacer-mediated synthesis of bis-spiroketal disaccharides: Nonsymmetrical furanose-pyranose difructose dianhydrides
Author keywords

Acetals; Difructose dianhydrides; Oligosaccharides; Spiro compounds; Spiroacetals
Indexed keywords

4,5 DI O BENZYL 3 O(3 BROMOMETHYLBENZYL) 1,2 O ISOPROPYLIDENE BETA DEXTRO FRUCTOPYRANOSE; FRUCTOSE; UNCLASSIFIED DRUG;
EID: 35748973267     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-991055     Document Type: Article
Times cited : (4)
References (52)
  • 21
    • 2542421693 scopus 로고    scopus 로고
    • vant Hooft, P. A. V.; Oualid, F. E.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H.; Leeuwenburgh, M. A. Org. Biomol. Chem. 2004, 2, 1395.
    • (b) vant Hooft, P. A. V.; Oualid, F. E.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H.; Leeuwenburgh, M. A. Org. Biomol. Chem. 2004, 2, 1395.
  • 41
    • 12944312239 scopus 로고    scopus 로고
    • The term 'contra-thermodynamic' designates diastereomers that are energetically strongly disfavored and, consequently, cannot be accessed under reversible kinetics or thermodynamic conditions. For examples of stereoselective syntheses of contra-thermodynamic spiroacetals, see: a
    • The term 'contra-thermodynamic' designates diastereomers that are energetically strongly disfavored and, consequently, cannot be accessed under reversible kinetics or thermodynamic conditions. For examples of stereoselective syntheses of contra-thermodynamic spiroacetals, see: (a) Takaoka, L. R.; Buckmelter, A. J.; LaCruz, T. E.; Rychnovsky, S. D. J. Am. Chem. Soc. 2005, 127, 528.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 528
    • Takaoka, L.R.1    Buckmelter, A.J.2    LaCruz, T.E.3    Rychnovsky, S.D.4
  • 45
    • 35748929545 scopus 로고    scopus 로고
    • 5-Di-O-benzyl-3-O-(3- bromomethylbenzyl)-1,2-O-isopropylidene-β-d-fructopyranose (13) To a solution of 1,3-bis(bromomethyl)benzene (1.99 g, 7.56 mmol, 2 equiv) in anhyd DMF (50 mL, NaH (60% in mineral oil, 378 mg, 9.45 mmol) was added and the suspension was stirred at r.t. for 15 min. Compound 10 12 (1.0 g, 3.78 mmol) was then added and the reaction mixture was further stirred for 24 h. Afterwards, Et2O (15 mL) and H2O (15 mL) were added, the organic layer was separated, washed with H2O (5 x 10 mL, dried (MgSO4, filtered, and concentrated. The resulting residue was purified by column chromatography (EtOAc-PE, 1:10) to yield 11 (955 mg, 57, Compound 11 (400 mg, 0.9 mmol) was dissolved in 60% aq AcOH (2.4 mL) and stirred at 45°C for 2 h. The reaction mixture was then diluted with H2O (5 mL) and extracted with EtOAc 4 x 4 mL, The com
    • 4), filtered, and concentrated. The resulting residue was purified by column chromatography (EtOAc-PE, 2:1) to give 12 (254 mg, 70%). Conventional benzylation of 12 (323 mg, 0.80 mmol) with NaH/BnBr afforded 13 (303 mg, 65%).
  • 46
    • 35748960116 scopus 로고    scopus 로고
    • General Procedure for the Preparation of (O- 6→O-3′)-Xylylene-Tethered Fructofuranose-Fructopyranose Derivatives (15 and 18) To a solution of 2,3-di-O-benzyl-1,2-O-isopropylidene-β-D- fructofuranose 149a (188 mg, 0.47 mmol) in dry DMF (3 mL, NaH (60% in mineral oil, 46 mg, 0.98 mmol) was added and the reaction mixture was stirred at r.t. for 1 h. A solution of 13 or 1713 (225 mg, 0.39 mmol) in anhyd DMF (4 mL) was then added, the reaction mixture was further stirred at r. t. for 3 h, quenched by addition of H2O (2 mL, concentrated and the resulting residue was purified by column chromatography using EtOAc-toluene (1:6) as eluent to give 15 (190 mg, 54, or 18 220 mg, 62
    • 2O (2 mL), concentrated and the resulting residue was purified by column chromatography using EtOAc-toluene (1:6) as eluent to give 15 (190 mg, 54%) or 18 (220 mg, 62%).
  • 47
    • 35748972214 scopus 로고    scopus 로고
    • 3N (0.1 mL) and concentrated. Column chromatography of the resulting residue (1:3 → 1:1 EtOAc-PE for 15; 1:5 → 1:2 EtOAc-PE for 18) afforded 16 (142 mg, 59%) or 19 (48.7 mg, 20.8%) and 20 (72.8 mg, 31.2%), respectively, as the only intramolecular reaction products.
    • 3N (0.1 mL) and concentrated. Column chromatography of the resulting residue (1:3 → 1:1 EtOAc-PE for 15; 1:5 → 1:2 EtOAc-PE for 18) afforded 16 (142 mg, 59%) or 19 (48.7 mg, 20.8%) and 20 (72.8 mg, 31.2%), respectively, as the only intramolecular reaction products.
  • 48
    • 35748932230 scopus 로고    scopus 로고
    • Selected data for 16: [α]D22 +10.1 (c 0.9, CHCl3, 1H NMR (500 MHz, CDCl3, δ, 4.16 (d, 1 H, J1a′,1b′, 11.6 Hz, H-1′a, 4.14 (m, 1 H, H-5, 4.00 (d, 1 H, J3,4, 2.5 Hz, H-3, 3.99 (m, 1 H, H-6a, 3.96 (d, 1 H, J1a,1b, 11.8 Hz, H-1a, 3.94 (dd, 1 H, J3′,4′, 9.5 Hz, J4′,5′, 3.2 Hz, H-4′, 3.83 (d, 2 H, J6a′,6b′, 12.0 Hz, H-6′a, H-1b, 3.74 (m, 1 H, H-6b, 3.72 (m, 1 H, H-5′, 3.61 (d, 1 H, H-3′, 3.60 (d, 1 H, H-6′b, 3.54 (dd, 1 H, J4,5, 7.5 Hz, H-4, 3.39 (d, 1 H, H-1′b, 13C NMR (125.7 MHz, CDCl3, δ, 102.3 (C-2, 95.9 (C-2′, 89.0 (C-3, 85.1 (C-4, 80.1 (C-5, 78.9 (C-3′, 78.6 (C-4′, 73.5 (C-5′, 75.8 (CH2Ph, 74.8 C-6
    • 10: C, 73.26; H, 6.40. Found: C, 73.07; H, 6.07.
  • 49
    • 35748934645 scopus 로고    scopus 로고
    • 2,4d
    • 2,4d
  • 51
    • 35748983071 scopus 로고    scopus 로고
    • Selected data for 19: [α]D22 +4.9 (c 0.8, CHCl3, 1H NMR (500 MHz, CDCl3, δ, 4.06 (d, 1 H, J6a,6b, 12.6 Hz, H-6a, 4.01 (brd, 1 H, J4,5, 8.7 Hz, H-5, 3.98 (dd, 1 H, J 3′,4′, 9.7 Hz, J4′,5′, 3.1 Hz, H-4′, 3.88 (d, 1 H, J3,4, 3.7 Hz, H-3, 3.86 (d, 1 H, J1a,1b, 13.7 Hz, H-1a, 3.84 (m, 1 H, H-6b, 3.72 (dd, H, J6a′,6b′, 11.5 Hz, J 5′,6a′, 3.0 Hz, H-6′a, 3.71 (m, 1 H, H-5′, 3.70 (d, 1 H, H-1b, 3.65 (d, 1 H, H-6′b, 3.61 (dd, 1 H, H-4, 3.55 (d, 1 H, H-3′, 3.39 (d, 1 H, J1a′,1b′, 12.0 Hz, H-1′a, 3.05 (d, 1 H, H-1′b, 13C NMR (125.7 MHz, CDCl3, δ, 102.0 (C-2, 95.2 (C-2′, 88.8 (C-3, 86.2 C-4, 79
    • 10: C, 73.26; H, 6.40. Found: C, 73.13; H, 6.48.
  • 52
    • 35748936930 scopus 로고    scopus 로고
    • Selected data for 20: [α]D22 +18.1 (c 1.0, CHCl3, 1H NMR (500 MHz, CDCl3, δ, 4.59 (d, 1 H, J1a,1b, 12.5 Hz, H-1a, 4.24 (dt, 1 H, J5,6b, 10.5 Hz, J5,6a, J 4,5, 4.5 Hz, H-5, 4.19 (d, 1 H, J1a′,1b′, 11.4 Hz, H-1′a, 4.15 (d, 1 H, J3′,4′, 7.9 Hz, H-3′, 4.13 (dd, 1 H, J3,4, 6.3 Hz, H-4, 4.05 (dd, 1 H, J6a′,6b′, 12.2 Hz, J 5′,6a′, 5.8 Hz, H-6′a, 3.87 (d, 1 H, H-3, 3.74 (dt, 1 H, J4′,5′, J 5′,6b′, 3.0 Hz, H-5′, 3.70 (d, 1 H, H-1b, 3.65 (dd, 1 H, J6a,6b, 10.5 Hz, H-6a, 3.60 (t, 1 H, H-6b, 3.52 (d, 1 H, H-1′b, 3.45 (dd, 1 H, H-6′b, 3.41 dd, 1 H, H-4′, 13C NMR
    • 10: C, 73.26; H, 6.40. Found: C, 73.13; H, 6.06.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.