, J = eight.9 Hz, 2H, Ar); HRMS calcd for C40H50O6SiNa+ [M+Na]+ 677.3269, identified 677.32567. 4.6. Basic procedure for desilylation of 4-C-substituted ribitols TBAF (1 M/THF; 0.4 mL, 0.4 mmol) was added to a stirred option of 10 (0.33 mmol) in THF (6 mL) at 0 (ice-bath). Right after 1 h, the volatiles had been evaporated as well as the resulting residue was washed with NaHCO3/H2O and extracted with EtOAc. The organic layer was then dried over Mg2SO4 and evaporated to provide crude residue which was column chromatographed (80 70 hexane/EtOAc). 4.six.1. 2,3-O-Isopropylidene-4-C-methyl-5-O-tritylribitol (11a)–Treatment of 10a (189 mg, 0.33 mmol) with TBAF employing procedure reported in section four.6 gave 11a (118 mg, 78 ): 1H NMR 1.35 (s, 3H, CH3), 1.40 (s, 3H, CH3), 1.49 (s, 3H, CH3), three.05 (d, J = 9.Author Manuscript Author Manuscript Author Manuscript Author ManuscriptJ Sulphur Chem. Author manuscript; offered in PMC 2017 February 24.Chbib et al.PageHz, 1H, H5), 3.32 (d, J = 9.0 Hz, 1H, H5), 3.58 (dd, J = five.two, 12.0 Hz, 1H, H1), 3.75 (dd, J = five.5, 12 Hz, 1H, H1), four.10sirtuininhibitor.20 (m, 1H, H2), 4.30 (d, J = 6.two Hz, 1H, H3), 7.25sirtuininhibitor.38 (m, 15H, Ar); 13C NMR 14.VEGF165 Protein supplier 21 (C1a), 25.17 27.28 (CMe2), 60.42 (C5), 61.43 (C1), 67.95 (CPh3), 68.38 (C4), 77.61 (C2), 79.10 (C3), 107.67 (CMe2), 127.27 127.97 128.62 143.43 (Ar); HRMS calcd for C28H32O5Na+ [M+Na]+ 471.2142; identified 471.2158. four.6.two. 2,3-O-Isopropylidene-4-C-hexyl-5-O-tritylribitol (11b)–Treatment of 10b (280 mg, 0.44 mmol) with TBAF making use of process reported in section four.6 gave 11b (145 mg, 87 ) as an viscous oil: 1H NMR 0.85 (t, J = 6.6 Hz, 3H, H6a), 1.NAMPT Protein supplier 30sirtuininhibitor.PMID:24516446 40 (m, 8H, H2asirtuininhibitorH5a), 1.25 (s, 3H, CH3), 1.40 (s, 3H, CH3), 1.50sirtuininhibitor.60 (m, 2H, H1a), two.91 (d, J = 9.3 Hz, 1H, H5), 3.20 (d, J = 9.3 Hz, 1H, H5), 3.30 (dd, J = five.0, 12.two Hz, 1H, H1), three.40 (dd, J = five.0, 12.0 Hz, 1H, H1), three.80 (q, J = five.8 Hz, 1H, H2), 4.15 (d, J = 5.eight Hz, 1H, H3), 7.25sirtuininhibitor.38 (m, 15H, Ar); 13C NMR 14.14 (C6a), 22.61, 23.06, 29.74, 31.83 (C2a 5a), 25.45 27.57 (CMe2), 36.05 (C1a), 61.88 (C1), 64.11 (C5), 74.35 (CPh3), 77.55 (C4), 79.14 (C2), 86.92 (C3), 107.21 (CMe2), 127.31 127.96 128.65 143.37 (Ar); HRMS calcd for C33H42O5Na+ [M+Na]+ 541.2924; located 541.2924. four.6.3. two,3-O-Isopropylidene-4-C-octyl-5-O-tritylribitol (11c)–Treatment of 10c (350 mg, 0.52 mmol) with TBAF applying process reported in section four.six gave 11c (200 mg, 84 ) as an viscous oil. 1H NMR 0.80 (t, J = six.6 Hz, 3H, H8a), 1.20sirtuininhibitor.30 (m, 12H, H2a-H7a), 1.29 (s, 3H, CH3), 1.40 (s, CH3), 1.50sirtuininhibitor.60 (m, 2H, H1a), 2.95 (d, J = 9.4 Hz, 1H, H5), three.25 (d, J = 9.three Hz, 1H, H5), 3.35 (dd, J = four.92, 12.2 Hz, 1H, H1), 3.45 (dd, J = five.four, 12.2 Hz, 1H, H1), 3.87sirtuininhibitor.94 (m, 1H, H2), 4.ten (d, J = five.8 Hz, 1H, H3), 7.25sirtuininhibitor.38 (m, 15H, Ar); 13C NMR 14.24 (C8a), 22.79, 23.17, 29.35, 29.68, 30.18, 32.00 (C2a 7a), 25.54 27.65 (CMe2), 36.13 (C1a), 61.94 (C1), 64.27 (C5), 74.41 (CPh3), 77.65 (C4), 79.28 (C2), 87.00 (C3), 107.27 (CMe2), 127.37, 128.03, 128.75 143.49 (Ar); HRMS calcd for C35H46O5Na+ [M+Na]+ 569.3237; discovered 569.3237. four.6.four. 2,3-O-Isopropylidene-4-C-vinyl-5-O-tritylribitol (11d)–Treatment of 10d (200 mg, 0.34 mmol) with TBAF making use of process reported in section four.six gave 11d (124 mg, 77 ) as a viscous oil: 1H NMR 1.35 (s, 3H, CH3), 1.37 (s, 3H, CH3), 3.38 (d, J = 11.2 Hz, 1H, H5), three.54 (d, J = 11.2 Hz, 1H, H5), three.58 (dd, J = 5.1, 11.three Hz, 1H, H1), three.90 (d.