68601-74-1

Usage

Uses

Used in Pharmaceutical Industry:
ALPHA1,3ALPHA1,6-MANNOTRIOSE, ALPHA-METHYL GLYCOSIDE is used as an inhibitor in the pharmaceutical industry for its ability to block the binding of phage G13 to its native receptor in the core region of lipopolysaccharides from Salmonella bacteria. This property makes it a potential candidate for the development of drugs targeting bacterial infections.
Used in Organic Synthesis:
In the field of organic synthesis, ALPHA1,3ALPHA1,6-MANNOTRIOSE, ALPHA-METHYL GLYCOSIDE serves as a valuable compound for the synthesis of various complex organic molecules. Its unique structure and functional groups make it a versatile building block for creating new compounds with potential applications in various industries.

InChI:InChI=1/C19H34O16/c1-30-17-15(29)16(35-19-14(28)12(26)9(23)6(3-21)33-19)10(24)7(34-17)4-31-18-13(27)11(25)8(22)5(2-20)32-18/h5-29H,2-4H2,1H3

Upstream product

• 228699-88-5 methyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->3)-[2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->6)]-2,4-di-O-acetyl-α-D-mannopyranoside 
• 176040-66-7 phenyl 2,3,4-tri-O-acetyl-1-thio-α-D-mannopyranoside 
• 80738-50-7 1,3,6-tri-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranose 
• 3254-16-8 3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 
• 81555-75-1 methyl 2-O-allyl-3-O-(tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 13242-53-0 acetobromomannose 
• 3162-96-7 methyl-4,6-O-phenylmethylene-α-D-mannopyranoside 
• 81600-89-7 methyl 2-O-allyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 82185-93-1 methyl 2-O-allyl-4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 73045-75-7 2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranosyl chloride 
• 79218-60-3 methyl 6-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-3-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 78880-16-7 methyl 2,4-di-O-benzyl-6-O-(2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 79218-66-9 3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl chloride 
• 79218-64-7 C₆₉H₇₈O₂₀ 

Downstream Products

• 72028-62-7 (2R,3S,4S,5S,6R)-2-((2R,3R,4S,5S,6S)-3,5-Dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 78962-39-7 methyl α-D-mannopyranosyl-(1→6)-α-D-mannopyranoside 

Relevant academic research and scientific papers

Synthesis of a library of 2-fluoro-2-deoxy-derivatives of the trimannoside methyl α-D-Man-(1 → 3)-[α-D-Man-(1 → 6)]-α-D-Man and the dimannosides methyl α-D-Man-(1 → 3)-α-D-Man and methyl α-D-Man-(1 → 6)-α-D-Man

A library of sixteen compounds, 1–16, comprising all (mono-, di-, and tri-) 2-fluoro-2-deoxy-derivatives of the N-glycan core trimannoside α-D-Man-(1 → 3)-[α-D-Man-(1 → 6)]-D-Man, including the corresponding 2-fluoro-2-deoxy disaccharide part structures and the non-fluorinated parent compounds, have been synthesized as their α-methyl glycosides for use as tools in 19F NMR-based lectin-carbohydrate interaction studies. Two methyl 2-fluoro-2-deoxy-mannoside acceptors, 21 (3-OH) and 22 (6-OH), were constructed and used in combination with the corresponding non-fluorinated mannose acceptors, 24 (6-OH) and 25 (3-OH), the 2-fluoro-2-deoxy mannosyl bromide donor 18 and the non-fluorinated bromide donor 23 to efficiently afford the target di-and trisaccharides (disaccharides, 2–3 steps, 47–66% overall yield; trisaccharides, 4 steps, 25–40% overall yield).

Anomalous Zemplen deacylation reactions of α- and β-D-mannopyranoside derivatives

Reaction of mono-, di-, and trisaccharide derivatives of methyl β-D- and octyl β-D-mannopyranosides bearing ester groups at isolated and non-isolated positions on the same molecule, under Zemplen conditions (catalytic amount of sodium methoxide in methanol) gave partially deacylated compounds, in which the O-acyl groups were retained at isolated sites. In the case of one disaccharide, all the benzoyl groups remained intact at the reducing end, while all the acetyl functions were removable from the nonreducing end. In another case, both isolated ester groups at positions 2 and 4 were retained at the reducing end. The isolated 2-O-acyl groups on methyl α-D-mannopyranoside compounds were more labile than on the corresponding β-mannosides under the same conditions. The mechanism of the reaction may be different for ester groups at isolated or non-isolated positions. In the latter case, acyl migration may take place and carry acyl groups into a less hindered position.

A combined intramolecular-intermolecular one-pot glycosylation approach for the synthesis of a branched trisaccharide

Intramolecular and intermolecular glycosidic couplings have been combined in a one-pot protocol for the synthesis of a branched trimannan.

Synthesis of highly branched oligomannosides. 3. Synthesis of trityl ethers of mannobiosides and mannotriosides as precursors for higher mannooligosaccharides [1,2]

Synthesis of mono- and ditrityl ethers of mannobiosides and mannotriosides as precursors for higher mannooligosaccharides is described. Advantage is taken of selective glycosylation of primary-secondary ditrityl ethers and selective removal of O-acetyl pr

Syntheses of model oligosaccharides of biological significance. Synthesis of methyl 3,6-di-O-(alpha-D-mannopyranosyl)-alpha-d-mannopyranoside and the corresponding mannobiosides.

Methyl 2-O-allyl-4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl) -alpha-D-mannopyranoside (12) was prepared in 90% yield by Helferich glycosylation of methyl 2-O-allyl-4,6-O-benzylidene-alpha-D-mannopyranoside (9) with tetra-O-acetyl

RECONSTRUCTION OF GLYCAN CHAINS OF GLYCOPROTEIN BRANCHING MANNOPENTAOSIDE AND MANNOHEXAOSIDE

Synthetic routes to the branching mannopentaoside 4 and mannohexaoside 5 are described employing properly protected mannobioside 13 as a key intermediate.

SYNTHESIS OF A BRANCHED D-MANNOPENTAOSIDE AND A BRANCHED D-MANNOHEXAOSIDE: MODELS OF THE INNER CORE OF CELL-WALL GLYCOPROTEINS OF Saccharomyces cerevisiae

Synthetic routes are discussed to the branched D-mannopentaoside methyl 6-O-(2,6-di-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-3-O-α-D-mannopyranosyl-α-D-mannopyranoside and D-mannohexaoside methyl 6-O-(2,6-di-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-3-O-(2

SYNTHESIS OF A BRANCHED D-MANNOPENTAOSIDE AND A BRANCHED D-MANNOHEXAOSIDE: MODELS OF THE OUTER CHAIN OF THE GLYCAN OF SOYBEAN AGGLUTININ

Synthetic routes are described to the D-mannopentaoside methyl 3-O-(3,6-di-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-6-O-α-D-mannopyranosyl-α-D-mannopyranoside and the D-mannohexaoside methyl 3-O-(3,6-di-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-6-O-(2-O-α-

SYNTHETIC STUDIES ON CELL SURFACE GLYCANS 3 BRANCHING PENTASACCHARIDES OF GLYCOPROTEIN

Synthetic routes for the branching pentasaccharides 4 and 5 of glycoproteins are described in a regio- and stereo-controlled way.