106988-70-9

Upstream product

• 149561-65-9 (-)-(2S,3S)-3-(Benzyloxy)-2-methyl-2,3-dihydro-4H-pyran-4-one 
• 117249-17-9 3,4-di-O-benzyl-L-rhamnal 
• 117249-16-8 1,5-anhydro-2,6-dideoxy-4-O-(phenylmethyl)-L-arabino-hex-1-enitol 

Downstream Products

• 106988-72-1 3-O-Acetyl-1,5-anhydro-4-O-benzyl-2,6-didesoxy-L-ribo-hex-1-enit 
• 158021-46-6 benzyl 4-O-benzyl-3-O-(4-O-benzyl-2,6-dideoxy-2-iodo-α-L-altropyranosyl)-2,6-dideoxy-2-iodo-α-L-altropyranoside 
• 106988-79-8 1,5-Anhydro-3,4-di-O-benzyl-2,6-didesoxy-L-ribo-hex-1-enit 
• 158052-13-2 benzyl 3-O-<3-O-(4-O-acetyl-3-O-benzyl-2,6-dideoxy-2-iodo-α-L-altropyranosyl)-4-O-benzyl-2,6-dideoxy-2-iodo-α-L-altropyranosyl>-4-O-benzyl-2,6-dideoxy-2-iodo-α-L-altropyranoside 

Relevant academic research and scientific papers

Palladium-Catalyzed One-Pot Stereospecific Synthesis of 2-Deoxy Aryl C-Glycosides from Glycals and Anilines in the Presence of tert-Butyl Nitrite

The palladium-catalyzed one-pot synthesis of 2,3-deoxy-3-keto aryl C-glycosides is achieved from glycals and anilines in the presence of tert-butyl nitrite and aqueous HBF 4 under mild conditions. This one-pot method stereospecifically provides α-and β-Aryl glycosides (≥19:1 by NMR) in good yields at room temperature. The configuration at the C-3 position in the glycal determines the anomeric selectivity (i.e., α or β) of the desired products.

Epimerization of glycal derivatives by a cyclopentadienylruthenium catalyst: Application to metalloenzymatic DYKAT

Epimerization of a non-anomeric stereogenic center in carbohydrates is an important transformation in the synthesis of natural products. In this study an epimerization procedure of the allylic alcohols of glycals by cyclopentadienylruthenium catalyst 1 is presented. The epimerization of 4,6-O-benzylidene-d-glucal 4 in toluene is rapid, and an equlibrium with its d-allal epimer 5 is established within 5 min at room temperature. Exchange rates for allal and glucal formation were determined by 1D 1H EXSY NMR experiments to be 0.055 s-1 and 0.075 s -1, respectively. For 4-O-benzyl-l-rhamnal 8 the epimerization was less rapid and four days of epimerization was required to achieve equilibration of the epimers at room temperature. The epimerization methodology was subsequently combined with acylating enzymes in a dynamic kinetic asymmetric transformation (DYKAT), giving stereoselective acylation to the desired stereoisomers 12, 13 , and 15. The net effect of this process is an inversion of a stereogenic center on the glycal, and yields ranging from 71% to 83% of the epimer were obtained.

Simple oxidation of 3-O-silylated glycals: Application in deblocking 3-0-protected glycals

A high yielding allylic oxidation of 3-O-siIylated glycals 5-10 with the reagent system PhI(OAc)2-TMSN3 is presented. The iodine(m) species generated under these conditions is a lot more effective for generating carbohydrate-derived 3-trialkylsiloxy-2,3-d