D-glucosamine-6-phosphate

Base Information

• Chemical Name: D-glucosamine-6-phosphate
• CAS No.: 3616-42-0
• Molecular Formula: C₆H₁₄NO₈P
• Molecular Weight: 259.153
• Hs Code.: 2922509090
• UNII: Y5ANY8MJ8J
• Nikkaji Number: J79.822C
• Wikidata: Q3109284
• Metabolomics Workbench ID: 53816
• Mol file: 3616-42-0.mol

Synonyms:D-glucosamine-6-phosphate;Y5ANY8MJ8J;aldehydo-D-glucosamine 6-phosphate;(2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxohexyl dihydrogen phosphate;[(2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxohexyl] dihydrogen phosphate;2-Amino-2-deoxy-D-glucose 6-(dihydrogen phosphate);D-Glucose, 2-amino-2-deoxy-, 6-(dihydrogen phosphate);2-Amino-2-deoxy-D-glucose 6-phosphate;2-amino-2-deoxy-aldehydo-D-glucose 6-(dihydrogen phosphate);Glucose-6-phosphate, 2-amino-2-deoxy-;UNII-Y5ANY8MJ8J;SCHEMBL19393;CHEBI:20995;Q3109284;C2CF8F90-5007-4659-BE40-6DEDD4F6B7D3;WURCS=2.0/1,1,0/[o2122h_2*N_6*OPO/3O/3=O]/1/;aldehydo-D-glucosamine 6-phosphate (open form, complete stereochemistry);(((2R,3S,4R,5R)-5-AMINO-3,4,6-TRIHYDROXYOXAN-2-YL)METHOXY)PHOSPHONIC ACID

Chemical Property of D-glucosamine-6-phosphate

Chemical Property:

• Vapor Pressure: 8.94E-20mmHg at 25°C
• Refractive Index: 1.585
• Boiling Point: 652.2 °C at 760 mmHg
• PKA: pKa 6.10 /8.14(H2O,t = 26.3,c=0.01,N2)(Approximate)
• Flash Point: 348.3 °C
• PSA: 172.51000
• Density: 1.749 g/cm³
• LogP: -2.43770
• Storage Temp.: −20°C
• Solubility.: Water (Slightly)
• XLogP3: -7.1
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 259.04570340
• Heavy Atom Count: 16
• Complexity: 267

Purity/Quality:

98%, ^*data from raw suppliers

D-Glucosamine 6-phosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C(C(C(C(C=O)N)O)O)O)OP(=O)(O)O
• Isomeric SMILES: C([C@H]([C@H]([C@@H]([C@H](C=O)N)O)O)O)OP(=O)(O)O
• Uses: Galactosamine-6-phosphate was identified as a component of the coat of the Bacillus megaterium QM B1551 spore. It was one of the main constituents of the outermost layer of the spore coat, but it was absent from the other integuments including the cortex. These findings suggest that galactosamine-6-phosphate comprises the phosphorus-containing skeleton structure of the spore coat.

Technology Process of D-glucosamine-6-phosphate

There total 7 articles about D-glucosamine-6-phosphate 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:

O1,O3,O4-triacetyl-2-amino-O6-phosphono-2-deoxy-β-D-glucopyranose → D-glucosamine-6-phosphate (6665-06-1,10236-82-5,26014-11-9,45170-71-6,3616-42-0)

Guidance literature:

With hydrogen bromide;

DOI:10.1021/ja01588a034

Reference yield:

2-deoxy-2-(4-methoxybenzylidene)amino-D-glucose (35946-64-6) → D-glucosamine-6-phosphate (6665-06-1,10236-82-5,26014-11-9,45170-71-6,3616-42-0)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine; acetic acid anhydride

2: acetone; aqueous hydrochloric acid

3: platinum; acetic acid / Hydrogenation

4: aqueous hydrobromic acid

With pyridine; hydrogenchloride; hydrogen bromide; acetic anhydride; acetic acid; acetone; platinum;

DOI:10.1021/ja01588a034

Reference yield:

O1,O3,O4-triacetyl-2-amino-O6-diphenoxyphosphoryl-2-deoxy-β-D-glucopyranose (71525-74-1) → D-glucosamine-6-phosphate (6665-06-1,10236-82-5,26014-11-9,45170-71-6,3616-42-0)

Guidance literature:

Multi-step reaction with 2 steps

1: platinum; acetic acid / Hydrogenation

2: aqueous hydrobromic acid

With hydrogen bromide; acetic acid; platinum;

DOI:10.1021/ja01588a034

upstream raw materials:

D-(+)-glucosamine hydrochloride

O¹,O³,O⁴-triacetyl-2-acetylamino-O⁶-phosphono-2-deoxy-β-D-glucopyranose

2-deoxy-2-(4-methoxybenzylidene)amino-D-glucose

O¹,O³,O⁴-triacetyl-2-amino-O⁶-diphenoxyphosphoryl-2-deoxy-β-D-glucopyranose

Downstream raw materials:

2-N-acetylamino-2-deoxy-D-glucose-6-phosphate

2-amino-2-deoxy-D-glucopyranose-1-(dihydrogen phosphate)