Benzyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside

Base Information

• Chemical Name: Benzyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside
• CAS No.: 13343-62-9
• Molecular Formula: C15H21NO6
• Molecular Weight: 311.335
• Hs Code.: 29389090
• European Community (EC) Number: 692-881-9
• DSSTox Substance ID: DTXSID80928117
• Nikkaji Number: J81.600K
• Wikidata: Q27458309
• ChEMBL ID: CHEMBL217900
• Mol file: 13343-62-9.mol

Synonyms:13343-62-9;BENZYL 2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE;N-((2S,3R,4R,5S,6R)-2-(Benzyloxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide;Benzyl 2-acetamido-2-deoxy-.alpha.-D-glucopyranoside;benzyl 2-acetamido-2-deoxy-a-D-Glucopyranoside;N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-phenylmethoxyoxan-3-yl]acetamide;Benzyl 2-(Acetylamino)-2-Deoxy-Alpha-D-Glucopyranoside;CHEMBL217900;SCHEMBL6814305;DTXSID80928117;SKOZFDIGKDPQBO-RYPNDVFKSA-N;AMY16285;CCG-43290;MFCD00070371;AKOS015924436;1-O-Benzyl-N-acetyl-alpha-D-glucosamine;DS-15737;CS-0090427;I11824;A806615;SR-01000633219-1;W-201098;Benzyl 2-Acetamido-2-deoxy- alpha -D-glucopyranoside;Q27458309;a-D-Glucopyranoside,phenylmethyl2-(acetylamino)-2-deoxy-;Benzyl 2-deoxy-2-[(1-hydroxyethylidene)amino]hexopyranoside;Phenylmethyl 2-(Acetylamino)-2-deoxy-alpha-D-glucopyranoside;.alpha.-D-Glucopyranoside, phenylmethyl 2-(acetylamino)-2-deoxy-;BBV

Chemical Property of Benzyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside

Chemical Property:

• Appearance/Colour: White Powder
• Vapor Pressure: 5.36E-15mmHg at 25°C
• Melting Point: 183-185 °C
• Refractive Index: 1.59
• Boiling Point: 594.9 °C at 760 mmHg
• PKA: 12.98±0.70(Predicted)
• Flash Point: 313.6 °C
• PSA: 108.25000
• Density: 1.34 g/cm³
• LogP: -0.46220
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 311.13688739
• Heavy Atom Count: 22
• Complexity: 360

Purity/Quality:

99% ^*data from raw suppliers

Benzyl 2-Acetamido-2-deoxy-a-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1OCC2=CC=CC=C2)CO)O)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1OCC2=CC=CC=C2)CO)O)O

Technology Process of Benzyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside

There total 53 articles about Benzyl 2-acetamido-2-deoxy-alpha-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: 100.0%

benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (10375-65-2,13318-46-2,13343-66-3,19374-72-2,33423-34-6,34029-78-2,41355-94-6,110911-57-4,141019-71-8) → benzyl 2-acetamido-2-deoxy-β-D-glucopyranoside (3055-51-4,3554-93-6,10380-86-6,13343-62-9,13343-67-4,19374-70-0,33423-30-2,33501-36-9,41355-95-7,86834-14-2,111003-11-3,347411-88-5)

Guidance literature:

With methanol; sodium methylate; at 20 ℃;

DOI:10.1021/ja020627c

Reference yield: 94.0%

N-Acetyl-D-glucosamine (7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4) + benzyl alcohol (100-51-6,185532-71-2) → benzyl 2-acetamido-2-deoxy-α-D-glucopyranoside (13343-62-9,347411-88-5)

Guidance literature:

With acetyl chloride; at 20 - 50 ℃; for 6h; Inert atmosphere;

DOI:10.1021/jo100456z

Reference yield: 81.6%

N-Acetyl-D-glucosamine (7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4) + benzyl alcohol (100-51-6,185532-71-2) → benzyl 2-deoxy-2-(N-acetylamino)-D-glucopyranoside (3055-51-4,3554-93-6,10380-86-6,13343-62-9,13343-67-4,19374-70-0,33423-30-2,33501-36-9,41355-95-7,86834-14-2,111003-11-3,347411-88-5)

Guidance literature:

With acetyl chloride; In methanol; at 20 - 25 ℃; for 24h; Cooling with ice;

upstream raw materials:

benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

2-acetamido-2-deoxy-D-glucose

benzyl alcohol

2-acetamido-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-glucitol

Downstream raw materials:

benzyl 2-acetamido-6-bromo-2,6-dideoxy-α-D-glucopyranoside

benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside

benzyl-2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-glucopyranoside

Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-<(R)-1-carboxyethyl>-α-D-glucopyranoside

Refernces

• 1、 Kusumoto, Shoichi,Imoto, Masahiro,Oguki, Tsuyoshi,Shiba, Tetsuo. "Synthesis of β(1-4)-Linked Disaccharides of N-Acetylglucosamine and3 N-Acetylmuramic Acid by Their Direct Condensation". . p. 1419 - 1424. Retrieved 1986.
• 2、 Mohammadnezhad, Gholamhossein,Mokhtari, Parisa. "Anti-cancer properties and catalytic oxidation of sulfides based on vanadium(V) complexes of unprotected sugar-based Schiff-base ligands". . . Retrieved 2022/01/26.
• 3、 Cheng, Wei-Chieh,You, Ting-Yun,Teo, Zhen-Zhuo,Sayyad, Ashik A.,Maharana, Jitendra,Guo, Chih-Wei,Liang, Pi-Hui,Lin, Chung-Shun,Meng, Fan-Chun. "Further Insights on Structural Modifications of Muramyl Dipeptides to Study the Human NOD2 Stimulating Activity". supporting information. p. 3836 - 3844. Retrieved 2020/10/21.