2-(Acetylamino)-2-deoxy-A-D-glucopyranose

Base Information

• Chemical Name: 2-(Acetylamino)-2-deoxy-A-D-glucopyranose
• CAS No.: 10036-64-3
• Deprecated CAS: 28905-09-1
• Molecular Formula: C8H15NO6
• Molecular Weight: 221.21
• Hs Code.: 29329900
• European Community (EC) Number: 233-115-1
• UNII: T13TI5GH3D
• DSSTox Substance ID: DTXSID20905442
• Nikkaji Number: J149.690E
• Wikidata: Q27120550
• NCI Thesaurus Code: C77375
• Metabolomics Workbench ID: 56548
• ChEMBL ID: CHEMBL1234669
• Mol file: 10036-64-3.mol

Synonyms:N-Acetyl-alpha-D-glucosamine;10036-64-3;2-Acetamido-2-deoxy-alpha-D-glucopyranose;alpha-GlcNAc;alpha-D-GlcNAc;2-(ACETYLAMINO)-2-DEOXY-A-D-GLUCOPYRANOSE;N-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide;N-((2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide;2-(acetylamino)-2-deoxy-alpha-D-glucopyranose;UNII-T13TI5GH3D;T13TI5GH3D;N-Acetyl-.alpha.-D-glucosamine;CHEBI:44278;EINECS 233-115-1;.alpha.-D-Glucopyranose, 2-(acetylamino)-2-deoxy-;2-Acetamido-2-deoxy-.alpha.-D-glucopyranose;Glucopyranose, 2-acetamido-2-deoxy-, .alpha.-D-;C8-H15-N-O6;1rdn;2-(Acetylamino)-2-deoxyhexopyranose #;NDG;SCHEMBL19899;CHEMBL1234669;DTXSID20905442;CCG-45087;MFCD00064359;AKOS015903840;DB03740;AC-19960;PS-11249;2-Acetamido-2-deoxy- alpha -D-glucopyranose;a-D-Glucopyranose,2-(acetylamino)-2-deoxy-;CS-0316763;FT-0772646;2-ACETAMIDO-2-DEOXY-.ALPHA.-D-GLUCOSE;C13970;C20328;EN300-7364454;.alpha.-D-glucopyranoside, 2-acetamido-2-deoxy-,;alpha-D-Glucopyranose, 2-(acetylamino)-2-deoxy-;2-Deoxy-2-[(1-hydroxyethylidene)amino]hexopyranose;2-DEOXY-2-ACETAMIDO-.ALPHA.-D-GLUCOPYRANOSE;SR-01000634877-1;W-200601;2-Acetamido-2-deoxy-alpha-D-glucopyranose, AldrichCPR;BRD-K41608622-001-01-2;Q27120550;GLUCOPYRANOSE, 2-ACETAMIDO-2-DEOXY-, .ALPHA.-D;WURCS=2.0/1,1,0/[a2122h-1a_1-5_2*NCC/3=O]/1/;alpha-N-Acetyl-D-glucosamine, N-[(2S,3R,4R,5S,6R)-6-(Hydroxymethyl)-2,4,5-trihydroxytetrahydro-2H-pyran-3-yl]acetamide, 2-(Acetylamino)-2-deoxy-alpha-D-glucopyranose

Chemical Property of 2-(Acetylamino)-2-deoxy-A-D-glucopyranose

Chemical Property:

• Appearance/Colour: White to off-white powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 211 °C
• Refractive Index: 1.576
• Boiling Point: 595.4 °C at 760 mmHg
• PKA: 12.04±0.70(Predicted)
• Flash Point: 313.9 °C
• PSA: 119.25000
• Density: 1.5 g/cm³
• LogP: -2.68670
• Storage Temp.: Refrigerator (+4°C)
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 221.08993720
• Heavy Atom Count: 15
• Complexity: 235

Purity/Quality:

98%, ^*data from raw suppliers

N-Acetyl-a-D-glucosamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1O)CO)O)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1O)CO)O)O
• Uses: N-Acetyl-a-D-glucosamine is a useful research chemical compound.

Technology Process of 2-(Acetylamino)-2-deoxy-A-D-glucopyranose

There total 139 articles about 2-(Acetylamino)-2-deoxy-A-D-glucopyranose 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%

(+)-D-glucosamine hydrochloride (1078691-95-8) + acetic anhydride (108-24-7) → 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)

Guidance literature:

With sodium hydrogencarbonate; In water; at 20 ℃; for 1.5h;

DOI:10.1002/ejoc.200300254

Reference yield:

N-[(2S,3R,4R,5S,6R)-2-(2-Chloro-ethylsulfanyl)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide (186135-39-7) → thirane (420-12-2) + N-acetyl-D-glucosamine (14131-68-1) + N-acetyl-D-glucosamine (10036-64-3) + N-[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-2-(2-hydroxy-ethylsulfanyl)-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide

Guidance literature:

With water; for 48h; Product distribution; Ambient temperature; other reaction times;

DOI:10.1135/cccc19961489

Reference yield:

4-nitrophenyl N-acetyl-β-D-glucosaminide (3459-18-5,50645-66-4) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 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)

Guidance literature:

With chitinase from Streptomyces griseus; In phosphate buffer; at 30 ℃; for 1h; pH=6.0; Product distribution; Enzymatic reaction;

DOI:10.1016/S0008-6215(99)00002-6

upstream raw materials:

2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline

N-acetyl neuraminic acid

uridine 5'-diphospho-N-acetylglucosamine

methanol

Downstream raw materials:

2-acetamido-2-deoxy-D-galacticol

2-acetylamino-O⁶-trityl-2-deoxy-D-galactose

2-acetylamino-2-deoxy-D-glucitol

methyl 2-acetamido-2-deoxy-β-D-galactopyranoside

Refernces

• 1、 Mukerjee,H.,Pal,P.R.. "-". . p. 2042 - 2043. Retrieved 1970.
• 2、 Hernandez,Ballou,Ballou. "Separation of yeast asparagine-linked oligosaccharides by high-performance anion-exchange chromatography.". . p. 1 - 11. Retrieved 1990.
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• 8、 Liu, Yihao,Jiang, Zhengqiang,Ma, Junwen,Ma, Shuai,Yan, Qiaojuan,Yang, Shaoqing. "Biochemical Characterization and Structural Analysis of a β- N-Acetylglucosaminidase from Paenibacillus barengoltzii for Efficient Production of N-Acetyl- d -glucosamine". . p. 5648 - 5657. Retrieved 2020.
• 9、 Tchoukoua, Abdou,Kuiate Tabopda, Turibio,Konga Simo, Ingrid,Uesugi, Shota,Ohno, Misa,Kimura, Ken-ichi,Kwon, Eunsang,Momma, Hiroyuki,Shiono, Yoshihito,Ngadjui, Bonaventure Tchaleu. "Albidosides H and I, two new triterpene saponins from the barks of Acacia albida Del. (Mimosaceae)". . p. 924 - 932. Retrieved 2018.
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