36954-63-9

Usage

Chemical Properties

Beige Solid

InChI:InChI=1/C28H39NO18/c1-11(30)29-21-24(41-15(5)34)22(19(9-38-12(2)31)45-27(21)44-18(8)37)47-28-26(43-17(7)36)25(42-16(6)35)23(40-14(4)33)20(46-28)10-39-13(3)32/h19-28H,9-10H2,1-8H3,(H,29,30)/t19?,20?,21-,22-,23-,24+,25-,26+,27+,28-/m1/s1

Upstream product

• 50605-11-3 (+)-2-acetamido-1,3-di-O-acetyl-2-deoxy-α-D-glucopyranoside 
• 32181-59-2 N-acetyllactosamine 
• 4307-58-8 N-acetyl-D-lactosamine 
• 108-24-7 acetic anhydride 
• 86231-83-6 2',3',4',6'-tetra-O-acetyl-1,6-anhydro-3-O-benzyl-N-acetyl-β-lactosamine 
• 86231-86-9 1,2',3',4',6,6'-hexa-O-acetyl-N-acetyl-α-lactosamine 
• 86520-63-0 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate 
• 73024-74-5 (+)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside 
• 79636-26-3 1,6-anhydro-2-azido-2-deoxy-4-O-(3-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranose 
• 79636-25-2 1,6-anhydro-2-azido-2-deoxy-4-O-(3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-β-D-glucopyranose 
• 79636-23-0 1,6:2,3-dianhydro-4-O-(3-O-benzyl-4,6-O-benzylidene-2-O-tosyl-α-D-glucopyranosyl)-β-D-mannopyranose 
• 79636-27-4 3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-4-O-(2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranose 
• 79636-24-1 1,6-anhydro-2-azido-2-deoxy-4-O-(3-O-benzyl-4,6-O-benzylidene-2-O-tosyl-α-D-glucopyranosyl)-β-D-glucopyranose 
• 78172-79-9 1,6:2,3-dianhydro-4-O-(4,6-O-benzylidene-2-O-tosyl-α-D-glucopyranosyl)-β-D-mannopyranose 

Downstream Products

• 212198-25-9 C₄₃H₆₀Cl₃NO₁₈ 
• 212198-12-4 C₃₉H₅₆Cl₃NO₁₆ 
• 212198-13-5 2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-3,5-diacetoxy-2-[(2R,3S,4R,5R,6R)-5-acetylamino-6-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-4-hydroxy-tetrahydro-pyran-3-yloxy]-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester 
• 212198-11-3 2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-acetylamino-6-benzyloxy-3-[(2S,3R,4S,5S,6R)-4-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-3,5-dihydroxy-tetrahydro-pyran-2-yloxy]-4-hydroxy-tetrahydro-pyran-2-ylmethyl ester 
• 53167-37-6 benzyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranoside 
• 53167-38-7 Benzyl-β-D-N-acetyllactosamine 
• 487000-70-4 phenyl 2-(N-acetylamino)-3,6-di-O-acetyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-seleno-β-D-glucopyranoside 

Relevant academic research and scientific papers

General and Chemoselective N-transacylation of secondary amides by means of perfluorinated anhydrides

A direct route: The N-transacylation of secondary amides to their perfluorinated analogues with the possibility of subsequent conversion into a normal amide is reported (see scheme). This reaction occurs in the presence of a variety of functional groups that are labile to the hydrolysis conditions required by classical N-transacylation. Chemical equation representation

Preparation of linear oligosaccharides by a simple monoprotective chemo-enzymatic approach

A monoprotective approach, involving acetyl ester as unique protective group in oligosaccharides synthesis, has been developed. Starting from peracetylated monosaccharides and glycals, by using an efficient and selective chemo-enzymatic 'one-pot' strategy (a regioselective hydrolysis catalyzed by immobilized lipases followed by a chemical acyl migration), different carbohydrate acceptors, only protected with acetyl ester, can be achieved. If combined with the use of an acetylated glycosyl donor, the glycosylation reaction with these glycosyl acceptors leads to peracetylated oligosaccharides. These compounds can be directly used as intermediates for the synthesis of glycopeptides used as antitumoral vaccines and, at the end of the process, can be easily fully deprotected in only one step. Thus, these key building blocks have been successfully used in glycosylation reactions for an efficient construction of peracetylated disaccharides, such as the biological relevant lactosamine, in multigram scale. Subsequently, glycosylation with the 3OH-tetraacetyl-α-d-galactose, used as carbohydrate acceptor, allowed the synthesis of a peracetylated N-trisaccharidic precursor of the lacto-N-neo-tetraose antigen. Extending this strategy to a 3OH-di-acetyl galactal, one peracetylated precursor of the T tumor-associated carbohydrate antigen has been synthesized. This efficient approach, characterized by the use of the acetyl ester as only protecting group during all the synthetical steps expected, represents an easy and efficient alternative to the classical synthetic methods in carbohydrate chemistry that involve several protecting group manipulation.

Novel synthetic approaches to manβ1-4GLCNAc and LeX units from N-acetyllactosamine

Regioselective protection of N-acetyllactosamine with triphenylmethyl (trityl) and pivaloyl groups afforded the corresponding 3, 2′, 4′-tri- and 2′,4′-dihydroxyl derivatives in a few steps, respectively; these derivatives were used efficiently for the syntheses of the title compounds from N-acetyllactosamine in 46% (7 steps) and 19% (8 steps) overall yields, respectively.

A chemoenzymatic approach towards moenomycin structural analogues

The trisaccharide moenomycin analogue 1c has been synthesized. One starting material was N-acetyllactosamine obtained by an enzyme-catalyzed transglycosylation. 1c differs from moenomycin degradation product 1a only in two positions of unit C. In contrast to 1a the synthetic 1c is antibiotically inactive.

Synthesis of 2-Acetamido-2-deoxy-4-O-β-D-galactopyranosyl-D-glucopyranose (N-Acethyllactosamine) Derivatives

In order to provide useful key intermediates for synthesises of complex oligosaccharides, anomeric 1,2',3',4',6,6'-hexa-O-acetyl-N-acetyllactosamines (8:α, and 9:β) and the corresponding 3-O-benzyl ethers (5:α, and 6:β) were synthesized.Condensation of 1,6-anhydro-3-O-benzyl-β-N-acetylglucosamine with acetobromogalactose by a conventional Koenigs-Knorr procedure, followed by selective acetolysis of the 1,6-anhydro-β-linkage, provided 5 and 6.Debenzylation of 5 and 6 gave 8 and 9, respectively.Keywords - Koenigs-Knorr synthesis; 1,6-anhydro-3-O-benzyl-β-N-acetylglucosamine; 1,6-anhydro-β-N-acetyllactosamine derivative; anomeric octaacetyllactosamine; anomeric heptaacetyllactosamine; anomeric 3-O-benzyl-heptaaetyllactosamine