Phenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside

Base Information

• Chemical Name: Phenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside
• CAS No.: 13089-21-9
• Molecular Formula: C20H25 N O9
• Molecular Weight: 423.42
• DSSTox Substance ID: DTXSID30425065
• Wikidata: Q82237816
• Mol file: 13089-21-9.mol

Synonyms:13089-21-9;PHENYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE;Phenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside;[(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-phenoxyoxan-2-yl]methyl acetate;HMS654I02;ChemDiv1_023762;DTXSID30425065;RTIVQWVVADQPHA-LASHMREHSA-N;AKOS001652168;SR-01000463043;SR-01000463043-1;Phenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside?

Chemical Property of Phenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside

Chemical Property:

• PSA: 126.46000
• LogP: 1.11240
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 10
• Exact Mass: 423.15293138
• Heavy Atom Count: 30
• Complexity: 632

Purity/Quality:

98%min ^*data from raw suppliers

Phenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1OC2=CC=CC=C2)COC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC2=CC=CC=C2)COC(=O)C)OC(=O)C)OC(=O)C

Technology Process of Phenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside

There total 19 articles about Phenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside 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: 93.0%

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) + phenol (108-95-2,27073-41-2) → 1-O-phenyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranose (13089-21-9)

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; for 0.75h; Ambient temperature;

Reference yield: 87.0%

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) + phenol (108-95-2,27073-41-2) → 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline (10378-06-0,20757-53-3,35954-65-5,123483-77-2,134308-33-1) + 1-O-phenyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranose (13089-21-9)

Guidance literature:

With tin(II) trifluoromethanesulfonate; 4 A molecular sieve; tetramethylurea; In dichloromethane; for 48h; Ambient temperature;

DOI:10.1016/S0040-4039(00)96690-5

Reference yield: 64.0%

acetic anhydride (108-24-7) + phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside (120498-97-7) → 1-O-phenyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranose (13089-21-9)

Guidance literature:

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside; With ethylenediamine; In butan-1-ol; at 80 ℃; for 16h;

acetic anhydride; With pyridine; for 16h;

DOI:10.1002/chem.200901830

upstream raw materials:

acetic anhydride

phenyl-(tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranoside)

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

phenol

Downstream raw materials:

phenyl 2-acetamido-2-deoxy-β-D-glucopyranoside

C₂₀H₂₄N₂O₁₁

4-nitrophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-mannopyranoside

o-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside

Refernces

• 1、 Kur'yanov,Priskoka,Chupakhina,Chirva. "A phase-transfer glucosamination of phenols catalyzed by polyethylene glycol". . p. 300 - 301. Retrieved 2005.
• 2、 Verdelet, Tristan,Benmahdjoub, Sara,Benmerad, Belkacem,Alami, Mouad,Messaoudi, Samir. "Copper-Catalyzed Anomeric O-Arylation of Carbohydrate Derivatives at Room Temperature". . p. 9226 - 9238. Retrieved 2019/08/12.
• 3、 Krenek, Karel,Simon, Petr,Weignerova, Lenka,Fliedrova, Barbora,Kuzma, Marek,Kren, Vladimir. "Facile synthesis of nitrophenyl 2-acetamido-2-deoxy-α-D- mannopyranosides from ManNAc-oxazoline". experimental part. p. 428 - 432. Retrieved 2012/05/05.