4-Methylumbelliferyl-beta-D-lactoside

Base Information

• Chemical Name: 4-Methylumbelliferyl-beta-D-lactoside
• CAS No.: 84325-23-5
• Molecular Formula: C22H28 O13
• Molecular Weight: 500.457
• Hs Code.: 29322090
• DSSTox Substance ID: DTXSID00470345
• Nikkaji Number: J931.597G
• Wikidata: Q72479944
• Mol file: 84325-23-5.mol

Synonyms:4-methylumbelliferyl beta-D-lactoside;4-methylumbelliferyl lactoside

Chemical Property of 4-Methylumbelliferyl-beta-D-lactoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: >178°C (dec.)
• Boiling Point: 830.319oC at 760 mmHg
• Flash Point: 286.047oC
• PSA: 208.74000
• Density: 1.658g/cm3
• LogP: -2.89570
• Storage Temp.: 2-8°C
• Solubility.: DMF: soluble
• XLogP3: -2.9
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 6
• Exact Mass: 500.15299094
• Heavy Atom Count: 35
• Complexity: 776

Purity/Quality:

98% ^*data from raw suppliers

4-Methylumbelliferyl b-D-lactoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)OC3C(C(C(C(O3)CO)OC4C(C(C(C(O4)CO)O)O)O)O)O
• Isomeric SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)O)O
• Uses: 4-Methylumbelliferyl-β-D-lactoside (CAS# 84325-23-5) is a fluorescent coumarin glycoside, used in the preparation of fluorescent probes for sialidases and sialyltransferases. 4-Methylumbelliferyl β-D-lactopyranoside has been used as a chromophoric substrate for cellobiohydrolase I (CBHI) in T. reesei. It has also been used as a substrate for cellobiohydrolase I (Cel7A), endoglucanase I (Cel7B) and β-glucosidase from fermented samples in enzymatic assay.

Technology Process of 4-Methylumbelliferyl-beta-D-lactoside

There total 3 articles about 4-Methylumbelliferyl-beta-D-lactoside 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: 85.0%

Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester (178450-89-0) → 4-methylumbelliferyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside (84325-23-5,66068-40-4)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 10h;

DOI:10.1021/ja0561690

Reference yield:

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) → 4-methylumbelliferyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside (84325-23-5,66068-40-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / BF₃*Et₂O; 4 Angstroem molecular sieves / CH₂Cl₂ / -10 - 0 °C

2: 85 percent / NaOMe / methanol / 10 h / 20 °C

With 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane;

DOI:10.1021/ja0561690

Reference yield:

2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-lactosyl trichloroacetimidate (92052-38-5,106256-89-7,126736-02-5,130703-21-8,132287-70-8,132287-71-9,139403-73-9,106256-81-9) → 4-methylumbelliferyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside (84325-23-5,66068-40-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / BF₃*Et₂O; 4 Angstroem molecular sieves / CH₂Cl₂ / -10 - 0 °C

2: 85 percent / NaOMe / methanol / 10 h / 20 °C

With 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane;

DOI:10.1021/ja0561690

upstream raw materials:

Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester

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

2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-lactosyl trichloroacetimidate

Downstream raw materials:

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

Refernces