350255-13-9

Upstream product

• 67337-61-5 3-deoxy-3-iodo-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 

Downstream Products

• 16667-96-2 O-[(3aR,5R,6S,6aR)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] methylsulfanylmethanethioate 
• 79378-71-5 (S)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose p-toluenesulfinate 
• 79378-71-5 (R)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose p-toluenesulfinate 
• 103526-79-0 1,2:5,6-Di-O-isopropylidene-3-O-(3'-phenylpropyl)-α-D-glucofuranose 
• 3219-55-4 N-benzylmethacrylamide 
• 103853-77-6 2-hydroxy-2-methyl-N-benzylpropanamide 
• 142061-49-2 2-(1,2:5,6-di-O-isopropylidene-D-glucofuranos-3-yloxy)-2-methyl-N-benzylpropanamide 
• 79384-20-6 (3aR,5R,6aR)-6-((2R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 
• 2774-28-9 3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose 
• 84730-39-2 3-O-(N,N-dimethylcarbamoyl)-1,2:5,6-di-O-isopropylidene-α-D-glucose 
• 4239-73-0 Bis-<1.2:5.6-di-O-isopropyliden-α-D-glucofuranose>-3.3'-thionocarbonat 
• 16713-76-1 Dimethyl-thiocarbamic acid O-[(3aR,5R,6S,6aR)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester 
• 4239-74-1 bis(1,2;5,6-di-O-isopropylidene-α-D-glucosyl)carbonate 
• 76548-23-7 tetrahydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[2,1-d]-1,3-oxazol-2-one 

Relevant academic research and scientific papers

(2-Benzyloxyphenyl)acetyl (BnPAc): A Participating Relay Protecting Group for Diastereoselective Glycosylation and the Synthesis of 1,2-trans Glycosyl Esters

The (2-benzyloxyphenyl)acetyl group has been identified as a new protecting group for hydroxyl functions. Various alcohols could be easily protected with high yields, and deprotection was achieved by a relay approach using Pd/H 2 in combination with 1,8-bis(dimethylamino)naphthalene, conditions that are orthogonal to ester groups. The new protecting group is stable in glycosylation reactions demonstrating an effective neighboring group participation leading to the exclusive formation of 1,2-trans glycosides and glycosyl esters.

A Mechanistic Study of the Photoreactions of Deoxy Iodo Sugars

Quantum yields of 0.31, 3.7, and 1.1 have been determined for the photochemical disappearance in heptane of 6-deoxy-6-iodo-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (1), 3-deoxy-3-iodo-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (2), and 3-deoxy-3-iodo-1,2:3,4-di-O-isopropylidene-α-D-glucofuranose (3), respectively.The major reaction for compounds 2 and 3 is epimerization at C-3, a reaction not observable for compound 1.Photochemical epimerization takes place in at least two ways.First, carbon-iodine bond homolysis followed by recombination of the radicalsproduced either regenerates the starting iodide or gives its C-3 epimer.Second, a chain reaction takes place in which the propagation step involves transfer of an iodine atom from the deoxy iodo sugar (2 or 3) to the carbon radical produced by carbon-iodine bond homolysis.In the presence of oxygen a new set of photoproducts is formed.These include enol esters, alcohols, and carbonyl compounds.