Water → HCID 23367341, compound

Reaction equation

I([O-])(=O)(=O)=O.[Na+].[C:7]([Si:11]([CH3:31])([CH3:30])[O:12][CH:13]1[CH2:18][CH:17]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:16][C:15]([OH:29])(CO)[CH2:14]1)([CH3:10])([CH3:9])[CH3:8].O>CO>[C:7]([Si:11]([CH3:31])([CH3:30])[O:12][CH:13]1[CH2:18][CH:17]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:16][C:15](=[O:29])[CH2:14]1)([CH3:10])([CH3:9])[CH3:8]

Participants

Procedure

Sodium periodate saturated water (28.5 mL) was added to the diol 15 (1.8 g, 4.7 mmol) in methanol (124 mL) at 0° C. The solution was stirred for 1 h, then poured into water and extracted with ether. The combined ether fractions were washed with brine, dried over anhydrous MgSO4, filtered and concentrated to give 16 (1.5 g, 90%). No further purification was required. 1H NMR (CDCl3, 500 MHz) 6 0.11 (s, 3H), 0.12 (s, 3H), 0.14 (s, 3H), 0.15 (s, 3H), 0.91 (s, 9H), 0.90 (s, 9H), 1.94 (m, 2H), 2.35 (m, 2H), 2.54 (m, 2H), 4.35 (m, 2×1H).