4-Methylumbelliferone N-acetyl neuraminic acid ketoside

Base Information

• Chemical Name: 4-Methylumbelliferone N-acetyl neuraminic acid ketoside
• CAS No.: 59322-44-0
• Molecular Formula: C₂₁H₂₅NO₁₁
• Molecular Weight: 467.43
• DSSTox Substance ID: DTXSID70974749
• Mol file: 59322-44-0.mol

Synonyms:2'-(4-methylumbelliferyl)-alpha-D-N-acetylneuraminic acid;4-methylcoumarin-7-yl-5-acetamido-3,5-dideoxy-alpha-glycero-galacto-2-nonulopyranosidonic acid;4-methylumbelliferone N-acetyl neuraminic acid ketoside;4-methylumbelliferyl alpha-ketoside of N-acetylneuraminic acid;4MU-NANA;MUNANA compound

Chemical Property of 4-Methylumbelliferone N-acetyl neuraminic acid ketoside

Chemical Property:

• Vapor Pressure: 7.71E-34mmHg at 25°C
• Boiling Point: 888.1°C at 760 mmHg
• Flash Point: 490.9°C
• PSA: 195.99000
• Density: 1.57g/cm³
• LogP: -0.97940
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 7
• Exact Mass: 467.14276061
• Heavy Atom Count: 33
• Complexity: 801

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)OC3(CC(C(C(O3)C(C(CO)O)O)NC(=O)C)O)C(=O)O
• Isomeric SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)O[C@@]3(C[C@@H]([C@H]([C@@H](O3)C([C@@H](CO)O)O)NC(=O)C)O)C(=O)O

Technology Process of 4-Methylumbelliferone N-acetyl neuraminic acid ketoside

There total 14 articles about 4-Methylumbelliferone N-acetyl neuraminic acid ketoside 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: 83.0%

methyl (4-methylcoumarin-7-yl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate (59361-08-9) → 4--methylcoumarin--7--yl 5--acetamido--3,5--dideoxy-α---D--glycero--D--galacto-2-nonulopyranosidonic acid (59322-44-0,88391-90-6)

Guidance literature:

methyl (4-methylcoumarin-7-yl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate; With sodium methylate; In methanol; for 1h; pH=8; Darkness;

With sodium hydroxide; In methanol; water; pH=11; Darkness;

DOI:10.1016/j.bmcl.2013.03.076

Reference yield:

sodium 4-methylumbelliferonate (5980-33-6) → 4--methylcoumarin--7--yl 5--acetamido--3,5--dideoxy-α---D--glycero--D--galacto-2-nonulopyranosidonic acid (59322-44-0,88391-90-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / aq. NaOH / benzyltriethylammonium chloride / CHCl₃ / 0.5 h / Heating

2: 1.) sodium methoxide, 2.) aq. NaOH / 1.) MeOH, RT, 2 h; 2.) RT, 0.5 h

With sodium hydroxide; sodium methylate; N-benzyl-N,N,N-triethylammonium chloride; In chloroform;

DOI:10.1016/0008-6215(90)84104-3

Reference yield:

Methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosyl chloride)onate (6770-41-8,59367-09-8,67670-69-3,132883-18-2,147129-74-6) → 4--methylcoumarin--7--yl 5--acetamido--3,5--dideoxy-α---D--glycero--D--galacto-2-nonulopyranosidonic acid (59322-44-0,88391-90-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / aq. NaOH / benzyltriethylammonium chloride / CHCl₃ / 0.5 h / Heating

2: 1.) sodium methoxide, 2.) aq. NaOH / 1.) MeOH, RT, 2 h; 2.) RT, 0.5 h

With sodium hydroxide; sodium methylate; N-benzyl-N,N,N-triethylammonium chloride; In chloroform;

DOI:10.1016/0008-6215(90)84104-3

upstream raw materials:

methyl (4-methylcoumarin-7-yl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester

sodium 4-methylumbelliferonate

Methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosyl chloride)onate

Downstream raw materials:

benzyl (4-methylcoumarin-7-yl-5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate

N-acetyl neuraminic acid

7-hydroxy-4-methyl-chromen-2-one

sialic acid