356067-93-1

Upstream product

• 100-39-0 benzyl bromide 
• 137915-37-8 1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose 
• 2873-29-2 D-glucal triacetate 
• 13265-84-4 D-glucal 

Downstream Products

• 356067-95-3 [(2R,3S,4R)-4-Benzyloxy-3-(4-methoxy-benzyloxy)-3,4-dihydro-2H-pyran-2-ylmethoxy]-triisopropyl-silane 
• 906650-47-3 Acetic acid (2R,3S,4R,5R,6S)-5-benzenesulfonylamino-4-benzyloxy-2-benzyloxymethyl-6-((2R,3S,4R)-4-benzyloxy-2-triisopropylsilanyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester 
• 356068-07-0 methyl (n-pentenyl 2-O-benzoyl-3-O-benzyl-4-O-para-methoxybenzyl-β-D-glucopyranosid)-uronate 
• 356068-02-5 (2S,3S,4R,5R,6R)-4-Benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 356068-08-1 methyl (n-pentenyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosid)-uronate 
• 356067-97-5 (2S,3S,4R)-4-Benzyloxy-3-(4-methoxy-benzyloxy)-3,4-dihydro-2H-pyran-2-carboxylic acid methyl ester 
• 356067-96-4 1,5-anhydro-3-O-benzyl-2-deoxy-4-O-(4-methoxybenzyl)-D-arabinohex-1-enitol 
• 210100-63-3 (3aR,5R,6R,7S,7aR)-7-Benzyloxy-5-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-ol 
• 444118-41-6 methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosiduronate 
• 906650-21-3 Acetic acid (2R,3S,4R,5R,6S)-5-benzenesulfonylamino-4-benzyloxy-2-benzyloxymethyl-6-[(2R,3S,4R)-4-benzyloxy-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-3,4-dihydro-2H-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester 
• 906650-20-2 Acetic acid (2R,3S,4R,5R,6S)-5-benzenesulfonylamino-4-benzyloxy-6-((2R,3S,4R)-4-benzyloxy-2-hydroxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-2-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 612845-04-2 3-O-benzyl-1,2-O-isopropylidene-6-O-triisopropylsilyl-α-D-glucopyranoside 
• 1054635-14-1 3-O-benzyl-4-O-t-butyldimethylsilyl-6-O-triisopropylsilyl-D-glucal 

Relevant academic research and scientific papers

One-pot conversion of glycals to cis-1,2-isopropylidene-α-glycosides

Described is a general method for the conversion of glycals to the corresponding 1,2-cis-isopropylidene-α-glycosides. Epoxidation of glycals with dimethyldioxirane followed by ZnCl2-catalyzed addition of acetone converted a variety of protected glycals into 1,2-cis-isopropylidene-α-glycosides in good yield. The reaction is compatible with a range of protecting groups, including esters, benzyl ethers, and silyl ethers, as well as free hydroxyl groups. This method has been applied to develop a synthesis of protected glucuronic acid 1, a key intermediate in the synthesis of glycosaminoglycans. Compound 1 was produced in seven steps and 32% overall yield.

Synthesis and transformations of D-glucuronic and L-iduronic acid glycals

D-Glucuronic acid glycals can be efficiently synthesized from diacetone glucose or tri-O-acetyl glycal and can be transformed into D-glucuronic acid donors and acceptors in high yields. Base catalyzed epimerization of D-glucuronic acid glycals provides access to the corresponding L-iduronic acid glycals. Both D-glucuronic and L-iduronic acid glycals were transformed into glycosylating agents for use in the synthesis of glycosaminoglycan oligosaccharides.