N-[(2R,3R,4R,5S,6R)-2-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

Base Information

• Chemical Name: N-[(2R,3R,4R,5S,6R)-2-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS No.: 4229-38-3
• Molecular Formula: C₈H₁₆N₂O₅
• Molecular Weight: 220.225
• Hs Code.: 2932990090
• DSSTox Substance ID: DTXSID101036106
• Nikkaji Number: J1.311.394G
• Wikidata: Q27098314
• Metabolomics Workbench ID: 37602
• Mol file: 4229-38-3.mol

Synonyms:18615-50-4;2-acetamido-2-deoxy-beta-D-glucopyranosylamine;N-Acetyl-beta-D-glucosaminylamine;4229-38-3;2-Acetamido-2-deoxy-beta-D-glucosylamine;2-Acetamido-2-deoxy-b-D-glucopyranosyl amine;2-Acetamido-2-deoxy-b-D-glucosylamine;N-Acetyl-b-glucosaminylamine;N-[(2R,3R,4R,5S,6R)-2-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide;N-acetyl-beta-glucosaminylamine;2-Acetamido-1-amino-1,2-dideoxy-beta-D-glucopyranose;114910-04-2;N-((2R,3R,4R,5S,6R)-2-AMINO-4,5-DIHYDROXY-6-(HYDROXYMETHYL)TETRAHYDRO-2H-PYRAN-3-YL)ACETAMIDE;112339-01-2;112339-04-5;.beta.-D-ribo-Hexopyranose, 1,6-anhydro-3-deoxy-2-S-methyl-4-O-(phenylmethyl)-2-thio-;.beta.-D-erythro-Hexopyranos-2-ulose, 1,6-anhydro-3-deoxy-4-O-(phenylmethyl)-, dimethyl acetal;1-Naphthalenediazonium, 4-[[4-[(4-nitro-2-sulfophenyl) amino]phenyl]azo]-6-sulfo-, chloride, reactio;N-acetyl-b-D-glucosaminylamine;SCHEMBL6036803;CHEBI:15947;DTXSID101036106;MFCD00057751;N-acetyl-beta-delta-glucosaminylamine;CS-0452428;2-Acetamido-2-deoxy-|A-D-glucopyranosylamine;C01239;W-202730;Q27098314;N-[2-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanamide

Chemical Property of N-[(2R,3R,4R,5S,6R)-2-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

Chemical Property:

• Vapor Pressure: 1.09E-14mmHg at 25°C
• Melting Point: 103-112°C dec.
• Refractive Index: 1.576
• Boiling Point: 556.2 °C at 760 mmHg
• PKA: 13.15±0.70(Predicted)
• Flash Point: 290.2 °C
• PSA: 125.04000
• Density: 1.43g/cm³
• LogP: -2.02000
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 220.10592162
• Heavy Atom Count: 15
• Complexity: 237

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYLAMINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: UVCB
• Canonical SMILES: CC(=O)NC1C(C(C(OC1N)CO)O)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1N)CO)O)O
• Uses: 2-Acetamido-2-deoxy-β-D-glucosylamine is used mainly for the synthesis of various 1-N-acyl derivatives which model the N-glycosylamine linkage of glycoproteins. This compound has been used as a building block in a variety of synthetic reactions.

Technology Process of N-[(2R,3R,4R,5S,6R)-2-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

There total 16 articles about N-[(2R,3R,4R,5S,6R)-2-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide 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%

2-N-acetylamido-2-deoxy-β-D-glucopyranosyl azide (29847-23-2) → 2-acetamido-2-deoxy-β-D-glucopyranosylamine (4229-38-3,102039-79-2,115350-20-4,133677-75-5,137493-97-1)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol;

DOI:10.1002/chem.201904688

Reference yield: 100.0%

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) → 2-acetamido-2-deoxy-β-D-glucopyranosylamine (4229-38-3,102039-79-2,115350-20-4,133677-75-5,137493-97-1)

Guidance literature:

With ammonium bicarbonate; at 42 ℃; for 36h;

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

Reference yield: 99.0%

2-acetamido-2-deoxy-β-D-glucopyranosylammonium carbamate → 2-acetamido-2-deoxy-β-D-glucopyranosylamine (4229-38-3,102039-79-2,115350-20-4,133677-75-5,137493-97-1)

Guidance literature:

In methanol; at 50 ℃;

DOI:10.1023/A:1015428720733

upstream raw materials:

N-acetyl-D-glucosamine

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

N-Acetyl-D-glucosamine

ethyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside

Downstream raw materials:

N-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-2-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-acetamide

(S)-N-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-2-benzyloxycarbonylamino-succinamic acid isobutyl ester

N^ω-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-N^α-(9-fluorenylmethyloxycarbonyl))-L-asparagine

N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-(4-hydroxy-3-nitrophenyl)acetamide

Refernces

• 1、 Ashhurst, Anneliese S.,Dowman, Luke J.,Fairbanks, Antony J.,Kwan, Ann,Larance, Mark,Li, Henry Y.,Payne, Richard J.,Wang, Xiaoyi,Watson, Emma E.. "Total Synthesis of Glycosylated Human Interferon-γ". supporting information. p. 6863 - 6867. Retrieved 2020/09/15.
• 2、 Du, Jing-Jing,Gao, Xiao-Fei,Xin, Ling-Ming,Lei, Ze,Liu, Zheng,Guo, Jun. "Convergent Synthesis of N-Linked Glycopeptides via Aminolysis of ω-Asp p-Nitrophenyl Thioesters in Solution". supporting information. p. 4828 - 4831. Retrieved 2016/10/14.