N-((2R,3R,4R,5R)-3,4,5,6-Tetrahydroxy-1-oxohexan-2-yl)acetamide

Base Information

• Chemical Name: N-((2R,3R,4R,5R)-3,4,5,6-Tetrahydroxy-1-oxohexan-2-yl)acetamide
• CAS No.: 1811-31-0
• Molecular Formula: C₈H₁₅NO₆
• Molecular Weight: 221.21
• Hs Code.: 29329990
• European Community (EC) Number: 217-321-9
• UNII: 833755V695
• Nikkaji Number: J199.634G
• Mol file: 1811-31-0.mol

Synonyms:1811-31-0;N-((2R,3R,4R,5R)-3,4,5,6-Tetrahydroxy-1-oxohexan-2-yl)acetamide;Galactose, 2-(acetylamino)-2-deoxy-;D-Galactose, 2-(acetylamino)-2-deoxy-;rel-N-Acetyl-D-galactosamine;N-[(2R,3R,4R,5R)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]acetamide;UNII-833755V695;833755V695;Galactosamine, N-acetyl-;SCHEMBL29837;AMY31299;CS-D0256;s3128;AKOS015837739;AKOS015901294;GALACTOSAMINE, N-ACETYL-, D-;D-Galactose,2-(acetylamino)-2-deoxy-;DS-5230;AC-32131;HY-33212;2-(ACETYLAMINO)-2-DEOXY-D-GALACTOSE;GALACTOSE, 2-ACETAMIDO-2-DEOXY-, D-;923F43AC-F163-4F64-95A2-69FD76AC3C0E;WURCS=2.0/1,1,0/[o2112h_2*NCC/3=O]/1/

Chemical Property of N-((2R,3R,4R,5R)-3,4,5,6-Tetrahydroxy-1-oxohexan-2-yl)acetamide

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 7.12E-19mmHg at 25°C
• Melting Point: 160-161 °C
• Refractive Index: 1.541
• Boiling Point: 636.4 °C at 760 mmHg
• PKA: 13.04±0.20(Predicted)
• Flash Point: 338.7 °C
• PSA: 127.09000
• Density: 1.423 g/cm³
• LogP: -2.84410
• Storage Temp.: 2-8°C
• Solubility.: H2O: 0.1 g/mL, clear, colorless
• Water Solubility.: Soluble in water at 50mg/ml
• XLogP3: -3.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 221.08993720
• Heavy Atom Count: 15
• Complexity: 221

Purity/Quality:

99%, ^*data from raw suppliers

N-Acetyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)NC(C=O)C(C(C(CO)O)O)O
• Isomeric SMILES: CC(=O)N[C@@H](C=O)[C@H]([C@H]([C@@H](CO)O)O)O
• Uses: N-Acetyl-D-galactosamine is the initial O-linked sugar to many serine and threonine residues in protein glycosylation.

Technology Process of N-((2R,3R,4R,5R)-3,4,5,6-Tetrahydroxy-1-oxohexan-2-yl)acetamide

There total 9 articles about N-((2R,3R,4R,5R)-3,4,5,6-Tetrahydroxy-1-oxohexan-2-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:

acetyl Coenzyme A + D-galactosamine (1948-54-5,2494-50-0,2636-92-2,3416-24-8,6915-39-5,7535-00-4,14307-02-9,14307-08-5,14307-09-6,14307-12-1,14307-14-3,14635-95-1,26315-48-0,27799-64-0,27799-65-1,69839-78-7,72904-60-0) → N-acetylgalactosamine (134-61-2,3615-17-6,4773-29-9,6813-82-7,7436-28-4,7512-17-6,20770-61-0,20880-43-7,20880-45-9,23583-38-2,23655-50-7,31022-50-1,50985-77-8,134451-94-8,149054-75-1,1811-31-0,282727-46-2,478518-83-1,127959-06-2,78393-48-3)

Guidance literature:

With human recombinant N-acetyltransferase; In aq. buffer; at 37 ℃; for 2h; pH=8; Enzymatic reaction;

DOI:10.1016/j.carres.2018.11.011

Reference yield:

2-acetamido-2-deoxy-D-glucose (7512-17-6,282727-46-2,478518-83-1,127959-06-2,78393-48-3) → N-acetylgalactosamine (134-61-2,3615-17-6,4773-29-9,6813-82-7,7436-28-4,7512-17-6,20770-61-0,20880-43-7,20880-45-9,23583-38-2,23655-50-7,31022-50-1,50985-77-8,134451-94-8,149054-75-1,1811-31-0,282727-46-2,478518-83-1,127959-06-2,78393-48-3)

Guidance literature:

With UDP-glucose 4-epimerase; N-acetylhexosamine 1-kinase; UDP-glucose-galactose 1-phosphate uridylyl transferase; ATP; magnesium chloride; at 30 ℃; for 120h; pH=6.5; aq. buffer; Enzymatic reaction;

DOI:10.1016/j.carres.2011.08.032

Reference yield:

heteropolysaccharide HPS4-2A from Radix Hedysari → L-arabinose (5328-37-0) + L-Rhamnose (3615-41-6,478518-52-4) + D-glucose (50-99-7) + D-Galactose (59-23-4) + N-acetylgalactosamine (134-61-2,3615-17-6,4773-29-9,6813-82-7,7436-28-4,7512-17-6,20770-61-0,20880-43-7,20880-45-9,23583-38-2,23655-50-7,31022-50-1,50985-77-8,134451-94-8,149054-75-1,1811-31-0,282727-46-2,478518-83-1,127959-06-2,78393-48-3)

Guidance literature:

With water; trifluoroacetic acid; at 121 ℃; for 3.5h;

DOI:10.1016/j.fitote.2013.05.011

upstream raw materials:

acetic anhydride

N-[(2R,3R,4R,5R,6R)-2-((S)-2,3-Dihydroxy-propoxy)-5-hydroxy-6-hydroxymethyl-4-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

α-L-Fuc-(1-3)-β-D-GalNAc-(1-3)-β-D-Gal-(1-4)-β-D-Gal-(1-3)-D-GalNAc-ol

2-acetamido-2-deoxy-D-glucose

Refernces

• 1、 Dang, Zilong,Feng, Demei,Liu, Xiaohua,Yang, Tao,Guo, Long,Liang, Jin,Liang, Jiandi,Hu, Fangdi,Cui, Fang,Feng, Shilan. "Structure and antioxidant activity study of sulfated acetamido- polysaccharide from Radix Hedysari". . p. 20 - 32. Retrieved 2013/10/22.
• 2、 Perepelov,Liu, Bin,Guo, Dan,Senchenkova,Shahskov,Feng, Lu,Wang, Lei,Knirel. "Structure elucidation of the O-antigen of Salmonella enterica O51 and its structural and genetic relation to the O-antigen of Escherichia coli O23". experimental part. p. 774 - 779. Retrieved 2012/01/19.