71806-86-5

Upstream product

• 69010-01-1 (2R*,3S*)-1,4-bis(benzyloxy)butane-2,3-diol 
• 77-76-9 2,2-dimethoxy-propane 
• 55904-12-6 ((4R,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol 
• 100-39-0 benzyl bromide 
• 141873-73-6 (1R,2R)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol 
• 141873-77-0 (1R,2R)-3-O-benzyl-1,2-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol 
• 141873-79-2 (1R,2R)-1,2-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol 
• 81801-08-3 4-O-benzyl-2,3-O-isopropylidene-aldehydo-D-erythrose 

Downstream Products

• 69010-01-1 (2R*,3S*)-1,4-bis(benzyloxy)butane-2,3-diol 
• 38279-61-7 meso-2,3-O-isopropylidene-1,4-di-O-(methanesulfonyl)butane-1,2,3,4-tetrol 

Relevant academic research and scientific papers

Desymmetrization of meso-1,2-Diols by a Chiral N,N-4-Dimethylaminopyridine Derivative Containing a 1,1′-Binaphthyl Unit: Importance of the Hydroxy Groups

We developed an acylative desymmetrization of meso-1,2-diols using a binaphthyl-based N,N-4-dimethylaminopyridine (DMAP) derivative 1h with tert-alcohol substituents. The reaction proceeds with a wide range of acyclic meso-1,2-diols and six-membered-ring meso-1,2-diols to provide a monoacylate selectively with a high enantiomeric ratio (er). Only 0.1 mol % of the catalyst facilitated the reaction within a short reaction time (3 h) to afford enantio-enriched monoacylated products in moderate to good yield. Several control experiments revealed that the tert-alcohol units of catalyst 1h play a significant role in achieving high catalytic activity, chemoselectivity of monoacylation, and enantioselectivity.

Effects of ring size and polar functional groups on the glutathione peroxidase-like antioxidant activity of water-soluble cyclic selenides

To elucidate the effects of ring structure and a substituent on the glutathione peroxidase- (GPx-) like antioxidant activities of aliphatic selenides, series of water-soluble cyclic selenides with variable ring size and polar functional groups were synthesized, and their antioxidant activities were evaluated by NADPH-coupled assay using H2O2 and glutathione (GSH) in water and also by NMR spectroscopy using H2O2 and dithiothreitol (DTTred) in methanol. Strong correlations were found among the GPx-like activity in water, the second-order rate constants for the oxidation of the selenides, and the HOMO energy levels calculated in water. The results support the conclusion that the oxidation process is the rate-determining step of the catalytic cycle. On the other hand, such correlations were not obtained for the activity observed in methanol. The optimal ring size was determined to be five. The type of substituent (NH2 2H) and the number can also control the activity, whereas the stereoconfiguration has only marginal effects on the activity in water. In methanol, however, the activity rank could not be explained by the simple scenarios applicable in water.

4-O-benzyl-2,3-O-isopropylidene-D-erythrose and -D-threose from 2,3-O-isopropylidene-D-glyceraldehyde via thiazole intermediates. Synthesis of 2-deoxykanosamine

The adduct derived from 2,3-O-isopropylidene-D-glyceraldehyde and 2-(trimethylsilyl)thiazole is readily converted into the title D-erythrose (50% overal yield) by selective protection of the hydroxy groups and cleavage of the thiazole ring; the D-threose