D, J = 11.six Hz, 1H, H5), three.71 (d, J = 11.6 Hz, H1, H5), four.55 (d
D, J = 11.six Hz, 1H, H5), 3.71 (d, J = 11.6 Hz, H1, H5), four.55 (d, J = five.six Hz, 1H, H2), four.90 (d, J = 5.6 Hz, 1H, H3); 13C NMR 16.42 (C1a), 25.81 26.76 (CMe2), 67.61 (C5), 77.82 (C2), 80.01 (C3), 86.35 (C4), 113.02 (CMe2), 174.46 (C1); HRMS (TOF) m/z calcd for C9H14O5Na+ [M+Na]+ 225.0733; identified 225.0734. 4.eight.2. two,3-O-Isopropylidene-4-C-hexyl-D-ribono-1,4-lactone (13b)–Treatment of 12b (31 mg, 0.06 mmol) with TFA applying procedure PFKM Protein Formulation reported in section four.eight (flash column chromatography; 80 hexane/EtOAc) gave 13b (12.five mg, 80 ): 1H NMR 0.80 (t, J = 6.6 Hz, 3H, H6a), 1.19sirtuininhibitor.21 (m, 8H, H2a 5a), 1.41 (s, 3H, CH3), 1.50 (s, 3H, CH3), 1.50sirtuininhibitor1.60 (m, 2H, H1a), 3.75 (d, J = 11.8 Hz, 1H, H5), 3.85 (d, J = 11.4 Hz, 1H, H5), 4.65 (d, J = five.six Hz, 1H, H2), four.96 (d, J = 5.6 Hz, 1H, H3); 13C NMR 14.06 (C6a), 22.47, 23.54, 29.42,Periostin Protein Purity & Documentation Author Manuscript Author Manuscript Author Manuscript Author ManuscriptJ Sulphur Chem. Author manuscript; offered in PMC 2017 February 24.Chbib et al.Page31.48 (C2a 5a), 25.79 26.78 (CMe2), 31.91 (C1a), 65.83 (C5), 77.20 (C3), 80.63 (C2), 89.73 (C4), 112.85 (CMe2), 172.67 (C1); HRMS (TOF) m/z calcd for C14H24O5Na+ [M +Na]+ 295.1516, found 295.1516. four.8.three. 2,3-O-Isopropylidene-4-C-octyl-D-ribono-1,4-lactone (13c)–Treatment of 12c (35 mg, 0.065 mmol) with TFA utilizing process reported in section four.eight gave 13c (16 mg, 75 ): 1H NMR 0.80 (t, J = 6.6 Hz, 3H, H8a), 1.30sirtuininhibitor.32 (m, 12H, H2a-H7a), 1.40 (s, 3H, CH3), 1.50 (s, 3H, CH3), 1.50sirtuininhibitor.60 (m, 2H, H1a), 3.75 (d, J = 11.6 Hz, 1H, H5), 3.85 (d, J = 11.six Hz, 1H, H5), four.65 (d, J = five.six Hz, 1H, H2), 4.95 (d, J = five.6 Hz, 1H, H3); 13C NMR 14.25 (CH3, C8a), 22.74, 23.64, 29.30, 29.41, 30.21, 31.27 (C2a 7a), 25.93 26.9 (CMe2), 31.98 (C1a), 65.92 (C5), 77.46 (C3), 79.91 (C2), 88.94 (C4), 113.0 (CMe2), 174.98 (C1); HRMS (TOF) m/z calcd for C16H28O5Na+ [M+Na]+ 323.1829; found 323.1915. 4.8.four. 2,3-O-Isopropylidene-4-C-vinyl-D-ribono-1,4-lactone (13d)–Treatment of 12d (30 mg, 0.065 mmol) with TFA working with procedure reported in section 4.8 (flash column chromatography; 80 hexane/EtOAc) gave somehow an unstable item 13d (5 mg, 35 ): 1H NMR 1.22 (s, 3H, CH3), 1.26 (s, 3H, CH3), 3.61 (d, J = 11.7 Hz, 1H, H5), 3.65 (d, J = 11.eight Hz, 1H, H5), 4.60 (d, J = 5.six Hz, 1H, H2), four.82 (d, J = 5.six Hz, 1H, H3), five.24 (d, J = 11.3 Hz, 1H, CH=CHH), five.34 (d, J = 17.5 Hz, 1H, C=CHH), five.71 (dd, J = 11.two, 17.5 Hz, 1H, CH=CHH); 13C NMR 25.87, 26.70 (CMe2), 66.37 (C5), 76.70 (C2), 80.01 (C3), 87.95 (C4), 113.29 (CMe2), 118.21 (CH=CH2), 130.53 (CH=CH2), 174.06 (C1); HRMS (TOF) m/z calcd for C10H14O5Na+ [M+Na]+ 237.0733; found 237.0733. 4.8.5. 2,3-O-Isopropylidene-4-C-4-methoxyphenyl-D-ribono-1,4-lactone (13e)– Remedy of 12e (70 mg, 0.13 mmol) with TFA utilizing process reported in section four.eight (flash column chromatography; 80 hexane/EtOAc) gave 13e (23 mg, 70 ): 1H NMR 1.22 (s, 3H, CH3), 1.25 (s, 3H, CH3), three.80 (s, 3H, CH3O), 3.85 (d, J = 12.3 Hz, 1H, H5), three.95 (d, J = 12.five Hz, 1H, H5), four.95 (d, J = 5.4 Hz, 1H, H2), five.15 (d, J = five.3 Hz, 1H, H3), six.82 (d, J = 8.eight Hz, 2H, Ar), 7.12 (d, J = 9.0 Hz, 2H, Ar); 13C NMR 25.83 26.65 (CMe2), 55.25 (CH3O), 68.50 (C5), 77.41 (C2), 80.57 (C3), 90.12 (C4), 112.93 (CMe2), 113.76, 126.17, 126.89, 159.33 (Ar); 174.86 (C1); HRMS (TOF) m/z calcd for C15H18O6Na+ [M+Na]+ 317.0996; identified 317.0982. 4.9. 2,3-O-Isopropylidene-4-C-hexyl-5-O-trityl-D-ribofuranose (14b) LiEt3BH (1M/THF, 0.18 mL, 0.18 mmol) was added dropwise to a so.
