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Volumn , Issue 5, 2009, Pages 0833-0837

The application of tert-butanesulfinamide in the asymmetric synthesis of the core structure of polyoxin and nikkomycin antibiotics

(3) Luo, Yong Chun a Zhang, Huan Huan a Xu, Peng Fei a

a LANZHOU UNIVERSITY (China)

Author keywords

(S) tert butanesulfinamide; Asymmetric synthesis; Nikkomycin; Polyoxin; Ribose

Indexed keywords

EID: 62349142396 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087949 Document Type: Article

Times cited : (10)

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- Procedure for the Synthesis of Compound 4: To a solution of n-BuLi (2.164 M in hexane, 1.39 mL, 3.0 mmol) at -78°C was added a solution of furan (245 mg, 3.6 mmol) in THF (5 mL, and the mixture was stirred at r.t. for 3 h. The mixture was then cooled to -78°C, and a solution of tert-butanesulfinyl imine 2 (0.5 M in THF, 4.0 mL, 2.0 mmol) was added via syringe over 10 min. The reaction mixture was stirred at -78°C for 3 h and quenched with a sat. NH4Cl solution (2 mL, The solvent was evaporated under reduced pressure and the residue was treated with H 2O (10 mL, The mixture was extracted with EtOAc, dried over anhyd Na2SO4 and concentrated. Flash chromatography of the residue (petroleum ether-EtOAc, 6:1) afforded compound 4 (96, as a white solid; mp 81-82°C; [α]D20 +3 (c, 0.5, CH2Cl2, IR KBr, 3235, 2935, 1462, 1377, 1210, 1157, 1
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- Spectroscopic Data of Compound 14: [α]D 20 +16 (c, 0.98, CHCl3, IR (KBr, 3299, 3065, 1750, 1696, 1239 cm-1. 1H NMR (400 MHz, CDCl3, δ, 9.09 (br s, 1 H, 7.30 (m, 5 H, 7.05 (s, 1 H, 5.94 (d, J, 5.2 Hz, 1 H, 5.93 (d, J, 8.8 Hz, 1 H, 5.53 (t, J, 5.6 Hz, 1 H, 5.28 (t, J, 6.0 Hz, 1 H, 5.10 (d, J, 4.0 Hz, 2 H, 4.84 (d, J, 3.9 Hz, 1 H, 4.38 (t, J, 4.4 Hz, 1 H, 3.80 (s, 3 H, 2.09 (s, 6 H, 1.88 (s, 3 H, 13C NMR 100 MHz, CDCl3, δ, 169.6, 169.5, 169.3, 163.3, 156.0, 135.8, 135.5, 128.5, 128.3, 128.1, 112.0, 87.5, 81.9, 77.2, 72.3, 69.7, 67.4, 60.3, 55.1, 52.9, 20.3, 12.4. HRMS: m/z [M, NH4, calcd for C24H 31N4O11: 551.1989; found: 551.1984
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