2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl azide

Base Information

• Chemical Name: 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl azide
• CAS No.: 13992-25-1
• Molecular Formula: C14H19 N3 O9
• Molecular Weight: 373.32
• Hs Code.: 29329990
• NSC Number: 272456
• Mol file: 13992-25-1.mol

Synonyms:2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl azide;a-D-Glucosyl azide, tetraacetate.;(3,4,5-triacetyloxy-6-azidooxan-2-yl)methyl acetate;13992-25-1;20379-61-7;MFCD00181721;MFCD05664724;MFCD08703928;SCHEMBL13904000;SCHEMBL19976657;NSC272456;STL480762;AKOS015912681;NSC-272456;BS-22680;SY072564;SY076719;SY249923;FT-0772753;.beta.-D-Glucopyranosyl azide,3,4,6-tetraacetate;A807599;beta-D-Glucopyranosyl Azide 2,3,4,6-Tetraacetate;Glucopyranosyl azide,3,4,6-tetraacetate, .beta.-D-;(3,4,5-triacetyloxy-6-azido-oxan-2-yl)methyl ethanoate;acetic acid (3,4,5-triacetyloxy-6-azido-2-oxanyl)methyl ester;azido-6-(ethanoyloxymethyl)tetrahydro-2h-pyran-3,4,5-triyl triethanoate;2-[(acetyloxy)methyl]-6-azidotetrahydro-2H-pyran-3,4,5-triyl triacetate (non-preferred name)

Chemical Property of 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl azide

Chemical Property:

• Appearance/Colour: White to beige crystalline powder
• Melting Point: 127-131 °C(lit.)
• Refractive Index: 1.5700 (estimate)
• Boiling Point: 502.57°C (rough estimate)
• PSA: 164.18000
• Density: 1.3271 (rough estimate)
• LogP: -0.16744
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 373.11212919
• Heavy Atom Count: 26
• Complexity: 617

Purity/Quality:

98% ^*data from raw suppliers

β-D-GlucopyranosylAzide2,3,4,6-Tetraacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 2-11
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)N=[N+]=[N-])OC(=O)C)OC(=O)C)OC(=O)C
• Uses: β-D-Glucopyranosyl Azide 2,3,4,6-Tetraacetate, is an intermediate used for the synthesis of Protein Tyrosine Phosphatase 1B inhibito1. It is used for the preparation of variously coupled conjugates of D-glucose via click chemistry for inhibition of glycogen phosphorylase.

Technology Process of 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl azide

There total 39 articles about 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl azide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

β-D-glucose pentaacetate (604-69-3) → 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate (13992-25-1)

Guidance literature:

With trimethylsilylazide; anhydrous tin tetrachloride; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/jo060409s

Reference yield: 100.0%

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (6919-96-6) → 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate (13992-25-1)

Guidance literature:

With sodium azide; In dimethyl sulfoxide; at 80 ℃;

DOI:10.1039/c9ob02081k

Reference yield: 100.0%

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate (13992-25-1)

Guidance literature:

With tetramethylguanidinum azide; In nitromethane; at 25 ℃; for 2.5h;

DOI:10.1016/S0040-4039(00)76995-4

upstream raw materials:

acetic anhydride

3,4,6-Tri-O-acetyl-β-D-glucopyranosylazid

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose

Downstream raw materials:

4,6-O-benzylidene-β-D-glucopyranosyl azide

1’-(4-phenyl-[1,2,3]-triazol-1-yl)-2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranose

2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine

1-N-benzylidene-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)imine

Refernces

• 1、 Berthold, Herwig J.,Franke, Stephan,Thiem, Joachim,Schotten, Theo. "Ex post glycoconjugation of phthalocyanines". . p. 3859 - 3862. Retrieved 2010.
• 2、 Neto, Virginie,Granet, Robert,Krausz, Pierre. "Novel class of non-ionic monocatenary and bolaform alkylglycoside surfactants. Synthesis by microwave-assisted glycosylation and olefin cross-metathesis or by 'click-chemistry': physicochemical studies". . p. 4633 - 4646. Retrieved 2010.
• 3、 Byrne, Joseph P.,Musembi, Pauline,Albrecht, Martin. "Carbohydrate-functionalized N-heterocyclic carbene Ru(ii) complexes: Synthesis, characterization and catalytic transfer hydrogenation activity". . p. 11838 - 11847. Retrieved 2019.
• 4、 Pavliak, Viliam,Kovac, Pavol. "A short synthesis of 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-β-D-glucopyranose and the corresponding α-glucosyl chloride from D-mannose". . p. 333 - 337. Retrieved 1991.
• 5、 Hu, Lei,Xu, Jintao,Zhang, Shixin,Zhao, Shuang. "Synthesis and comparative study of emulsifying and biological properties of triazolated glucolipids". . . Retrieved 2020.
• 6、 Tsoulougian, Veronika,Psykarakis, Emmanuel E.,Gimisis, Thanasis. "Synthesis of biurets: Via TMSNCO addition to 1-aminosugars: Application in the de novo synthesis of dC oxidation products". . p. 973 - 981. Retrieved 2019.
• 7、 Bonomi, Paolo,Attieh, Mira Daoud,Gonzato, Carlo,Haupt, Karsten. "A New Versatile Water-Soluble Iniferter Platform for the Preparation of Molecularly Imprinted Nanoparticles by Photopolymerisation in Aqueous Media". . p. 10150 - 10154. Retrieved 2016.
• 8、 Vrbata, David,Dor?ovic, Vladimír,Seitsonen, Jani,Ruokolainen, Janne,Janou?ková, Olga,Uchman, Mariusz,Matějí?ek, Pavel. "Preparation of membrane-mimicking lamellar structures by molecular confinement of hybrid nanocomposites". . p. 2900 - 2903. Retrieved 2019.
• 9、 Orth, Ronald,Pitscheider, Maximilian,Sieber, Stephan A.. "Chemical probes for labeling of the bacterial glucosaminidase nagZ via the huisgen cycloaddition". . p. 2201 - 2206. Retrieved 2010.
• 10、 Al-Masoudi, Najim A.,Al-Soud, Yaseen A.. "Synthesis of 1′-β-D-glucopyranosyl-1,2,3-triazole-4,5-dimethanol-4,5-bis (isopropylcarbamate) as potential antineoplastic agent". . p. 4021 - 4022. Retrieved 2002.