2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl Azide

Base Information

• Chemical Name: 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl Azide
• CAS No.: 6205-69-2
• Molecular Formula: C14H20N4O8
• Molecular Weight: 372.335
• Hs Code.: 29329990
• European Community (EC) Number: 612-938-3
• DSSTox Substance ID: DTXSID901160654
• Nikkaji Number: J478.536C
• Mol file: 6205-69-2.mol

Synonyms:6205-69-2;2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl Azide;2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-glucopyranosyl azide;Azido 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-glucopyranoside;[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-azidooxan-2-yl]methyl acetate;SCHEMBL15938748;C14H20N4O8;DTXSID901160654;2-Acetamido-2-deoxy-b-D-glucopyranosyl azide 3,4,6-triacetate;GEO-03200;MFCD00216968;AKOS040768954;GS-0678;T71131;A833554;1-Azido-3-O,4-O,6-O,N-tetraacetyl-1-deoxy-beta-D-glucosamine;Azido 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-?-D-glucopyranoside;2-acetamido-3,4,6-tri-O-acetyl-1-azido-1,2-dideoxy-beta-d-glucopyranose;Azido 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl- beta -D-glucopyranoside;beta-D-Glucopyranosyl azide, 2-(acetylamino)-2-deoxy-, 3,4,6-triacetate;[(2R,3S,4R,5R,6R)-3,4-BIS(ACETYLOXY)-6-AZIDO-5-ACETAMIDOOXAN-2-YL]METHYL ACETATE;[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetoxy-6-azido-tetrahydropyran-2-yl]methyl acetate;2-Acetamido-2-deoxy-beta-D-glucopyranosyl azide 3,4,6-triacetate, >=98.0% (HPLC);(2R,3S,4R,5R,6R)-5-acetamido-2-(acetoxymethyl)-6-azidotetrahydro-2H-pyran-3,4-diyl diacetate;InChI=1/C14H20N4O8/c1-6(19)16-11-13(25-9(4)22)12(24-8(3)21)10(5-23-7(2)20)26-14(11)17-18-15/h10-14H,5H2,1-4H3,(H,16,19)/t10-,11-,12-,13-,14-/m1/s1

Chemical Property of 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl Azide

Chemical Property:

• Appearance/Colour: white solid
• Melting Point: 128-130 °C
• Refractive Index: 1.6200 (estimate)
• Boiling Point: 501.81°C (rough estimate)
• PSA: 166.98000
• Density: 1.2964 (rough estimate)
• LogP: -0.20354
• Storage Temp.: Freezer
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 9
• Exact Mass: 372.12811361
• Heavy Atom Count: 26
• Complexity: 618

Purity/Quality:

98%, ^*data from raw suppliers

Azido 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-b-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(OC1N=[N+]=[N-])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]1N=[N+]=[N-])COC(=O)C)OC(=O)C)OC(=O)C

Technology Process of 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl Azide

There total 30 articles about 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl 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%

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide (6205-69-2)

Guidance literature:

With sodium azide; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; In dichloromethane;

DOI:10.1016/S0040-4039(00)02286-3

Reference yield: 98.0%

2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl chloride (3068-34-6,41355-44-6,51236-40-9,74081-14-4,79897-03-3,100759-09-9,109581-83-1,38874-23-6) → 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide (6205-69-2)

Guidance literature:

With sodium azide; for 8h;

DOI:10.1080/07328300802161897

Reference yield: 98.0%

2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3) → 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide (6205-69-2)

Guidance literature:

With trimethylsilylazide; silver perchlorate; tin(IV) chloride; In dichloromethane; toluene; for 7h;

DOI:10.1246/cl.1994.247

upstream raw materials:

2-isopropylidenamino-2-deoxy-β-D-glucopyranosyl azide

acetic anhydride

3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranosyl azide

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

Downstream raw materials:

2-N-acetylamido-2-deoxy-β-D-glucopyranosyl azide

N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)triphenylphosphine imide

3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yl)-5-phenyl-3H-[1,2,3]triazole-4-carboxylic acid 2-(7-isopropyl-1-methyl-azulen-4-yl)-ethyl ester

1-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yl)-5-phenyl-1H-[1,2,3]triazole-4-carboxylic acid 2-(7-isopropyl-1-methyl-azulen-4-yl)-ethyl ester