65827-57-8

Usage

Uses

Used in Organic Synthesis:
1,2,6-Tri-O-acetyl-3,4-di-O-benzyl-a-D-mannopyranose is used as a key intermediate in the synthesis of complex carbohydrates and their derivatives. Its unique structural features, including the acetyl and benzyl protecting groups, allow for selective reactions and the formation of a wide range of carbohydrate structures with diverse functional groups.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,2,6-Tri-O-acetyl-3,4-di-O-benzyl-a-D-mannopyranose is used as a building block for the synthesis of glycoconjugates, which are compounds consisting of carbohydrates covalently linked to other biomolecules, such as proteins or lipids. These glycoconjugates play crucial roles in various biological processes, including cell recognition, signaling, and immune responses. The synthesis of these complex structures often requires the use of versatile carbohydrate building blocks like 1,2,6-Tri-O-acetyl-3,4-di-O-benzyl-a-D-mannopyranose.
Used in Material Science:
1,2,6-Tri-O-acetyl-3,4-di-O-benzyl-a-D-mannopyranose is also used in the development of carbohydrate-based materials, such as polymers, gels, and coatings. These materials exhibit unique properties, such as biocompatibility, biodegradability, and specific recognition abilities, making them suitable for various applications, including drug delivery, tissue engineering, and sensors.

InChI:InChI=1/C26H30O9/c1-17(27)30-16-22-23(31-14-20-10-6-4-7-11-20)24(32-15-21-12-8-5-9-13-21)25(33-18(2)28)26(35-22)34-19(3)29/h4-13,22-26H,14-16H2,1-3H3

Upstream product

• 16697-49-7 3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose 
• 108-24-7 acetic anhydride 
• 73045-75-7 2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranosyl chloride 
• 29073-91-4 (3aS,5R,6S,7aS)-5-Hydroxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol 
• 79218-92-1 1,2-O-(1-methoxyethylidene)-6-O-trityl-β-D-mannopyranose 
• 100-39-0 benzyl bromide 
• 65827-63-6 (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2,3-diol 
• 79218-91-0 3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-6-O-trityl-β-D-mannopyramose 

Downstream Products

• 138566-31-1 Acetic acid (2R,3S,4S,5R,6R)-6-acetoxymethyl-4,5-bis-benzyloxy-2-ethylsulfanyl-tetrahydro-pyran-3-yl ester 
• 73045-75-7 2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranosyl chloride 
• 88493-87-2 2,6-di-O-acetyl-3,4-di-O-benzyl-β-D-mannopyranosyl bromide 
• 100759-62-4 2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranosyl bromide 
• 79218-89-6 methyl 2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranoside 
• 79218-88-5 methyl 2,6-di-O-acetyl-3,4-di-O-benzyl-β-D-mannopyranoside 
• 57783-73-0 methyl 3,4-di-O-benzyl-α-D-mannopyranoside 
• 79218-74-9 methyl 3,4-di-O-benzyl-β-D-mannopyranoside 
• 65827-63-6 (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2,3-diol 
• 79218-90-9 6-O-acetyl-3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 
• 79218-86-3 methyl 2,6-di-O-<2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl>-3,4-di-O-benzyl-α-D-mannopyranoside 
• 94537-68-5 Benzyl-6-O-benzoyl-3,4-di-O-benzyl-α-D-mannopyranosid 
• 94537-67-4 Benzyl-6-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranosid 
• 86173-12-8 Benzyl 2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranoside 

Relevant academic research and scientific papers

Synthesis of α-D-glucopyranosyl-(1-3)-α-D-mannopyranosyl-(1-7)-4- methylumbelliferone, a fluorogenic substrate for endo-α-1,2-mannosidase

α-D-Glucopyranosyl-(1-3)-α-D-mannopyranosyl-(1-7)-4- methylumbelliferone (Glc-Man-Muf) was synthesized as a potential fluorogenic substrate for endo-α-1,2-mannosidase. The synthesis was designed in a convergent way. The glucose donor ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-glucopyranoside and the mannose acceptor 1,2:4,6-di-O-isopropylidene-β-D-mannopyranose were coupled in the presence of N-iodosuccinimide and trifluoromethane-sulfonic acid to yield the corresponding disaccharide derivative. After conversion into peracetylated α-D-glucopyranosyl-(1-3)-α-D-mannopyranose the disaccharide was attached to 4-methylumbelliferone using the Helferich method. After separation of the desired isomer, deacetylation yielded the title compound. Glc-Man-Muf was used as a substrate in endomannosidase assays with rat liver Golgi preparations as an enzyme source (in the presence of the α-glucosidase inhibitor deoxynojirimycin). The degradation of Glc-Man-Muf was linear with protein up to 300 μg and with time up to 2 h. Vmax and Km were determined to be 0.17 nmol/mg × h and 3.7 mM, respectively.

SYNTHESIS OF A PEPTIDYLDIMANNOSYL PHOSPHATE: FRAGMENT OF THE VARIANT-SPECIFIC SURFACE GLYCOPROTEIN MEMBRANE ANCHOR FROM TRYPANOSOMA BRUCEI

Condensation of protected β-benzyl-aspartate 4 with 2-amino-ethanol, subsequent deprotection of the amino function and coupling with N,N'-di-benzyloxycarbonyl-lysine (7) afforded the peptidyl alcohol 8.Glycosylation of methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside (11) by ethyl 2,6-di-O-benzoyl-3,4-di-O-benzyl-1-thio-α-D-mannopyranoside (14) gave, after debenzoylation and protection of the 2'-hydroxyl function, the suitably protected dimannoside 21.Phosphitylation of 21 with benzyloxy-bis-(N,N-diisopropylamino)phosphine (18) followed by the addition of 8 gave, after oxidation and subsequent hydrogenolysis of the benzyl groups, the title compound in a good yield.

SYNTHESIS OF A MODEL OF AN IMMER CHAIN OF CELL-WALL PROTEOHETEROGLYCAN ISOLATED FROM Piricularia oryzae: BRANCHED D-MANNOPENTAOSIDES

Efficient syntheses are described of the branched D-mannopentaosides methyl 2,6-di-O-(2-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-α-D-mannopyranoside and methyl 2,4-di-O-(2-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-α-D-mannopyranoside, starting from the gly