129796-70-9

Upstream product

• 80-97-7 Cholestanol 
• 86795-39-3 (2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-chloro-6-methyltetrahydro-2H-pyran 
• 131897-04-6 phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-rhamnopyranoside 

Relevant academic research and scientific papers

New Synthetic Methods and Reagents for Complex Carbohydrates. VIII. Steroselective α- and β-Mannopyranoside Formation from Glycosyl Dimethylphosphinothioates with the C-2 Axial Benzyloxyl Group

The reactions of mannopyranosyl dimethylphosphinothioates and alcohols using silver perchlorate as an activator in the presence of molecular sieves 4A in benzene at room temperature gave the 1,2-trans-α-mynnopyranosides in good yields.On the other hand, 1

The 3,4-O-Carbonate Protecting Group as a β-Directing Group in Rhamnopyranosylation in Both Homogeneous and Heterogeneous Glycosylations As Compared to the Chameleon-like 2,3-O-Carbonates

It is demonstrated that the β-selectivity observed in the insoluble silver salt mediated couplings of 2,3-O-carbonate-protected rhamnosyl bromides is uniquely due to the heterogeneous nature of the reaction. In homogeneous solution these same donors are α-selective, a fact that is attributed to the half-chair conformation of these substances which reduces the energy barrier to oxacarbenium ion formation. It is suggested that the 2,3-O-carbonate group be dubbed torsionally arming in the manno- and rhamnopyranose series. When the carbonate group is removed to the 3,4-O-position a β-selective system is formed, in both homogeneous and heterogeneous conditions, and it is demonstrated that this selectivity arises from the combination of the electron-withdrawing nature of the carbonate and its inability to take part in neighboring participation.

α-Selective thermal glycosidation of rhamnosyl and mannosyl chlorides

Stereoselective thermal glycosylation of a variety of alcohols with 2,3,4-tri-O-benzylα-L-rhamnopyranosyl chloride and 2,3,4,6-tstra-O-benzyl-α-D-mannopyranosyl chloride have achieved to give α-glycosides in high selectivity.