4-Methylumbelliferyl2,3,4,6-tetra-O-acetyl-a-D-glucopyranoside

Base Information

• Chemical Name: 4-Methylumbelliferyl2,3,4,6-tetra-O-acetyl-a-D-glucopyranoside
• CAS No.: 67945-53-3
• Molecular Formula: C24H26O12
• Molecular Weight: 506.463
• Mol file: 67945-53-3.mol

Synonyms:4-Methylumbelliferyl 2,3,4,6-tetrα-O-acetyl-α-D-glucopyranoside

Chemical Property of 4-Methylumbelliferyl2,3,4,6-tetra-O-acetyl-a-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 128-130°C
• Boiling Point: 607.772°C at 760 mmHg
• Flash Point: 259.546°C
• PSA: 153.87000
• Density: 1.375g/cm³
• LogP: 1.56330

Purity/Quality:

98% ^*data from raw suppliers

4-Methylumbelliferyl2,3,4,6-Tetra-O-acetyl-α-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Methylumbelliferyl 2,3,4,6-Tetra-O-acetyl-α-D-glucopyranoside (cas# 67945-53-3) is a compound useful in organic synthesis.

Technology Process of 4-Methylumbelliferyl2,3,4,6-tetra-O-acetyl-a-D-glucopyranoside

There total 2 articles about 4-Methylumbelliferyl2,3,4,6-tetra-O-acetyl-a-D-glucopyranoside 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: 45.0%

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) + β-D-glucose pentaacetate (604-69-3) → 4′-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (67909-25-5) + 4′-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside (67945-53-3) + 4-methylumbelliferyl acetate (2747-05-9)

Guidance literature:

With dmap; boron trifluoride diethyl etherate; In 1,2-dichloro-ethane; at 60 ℃; for 5h; stereoselective reaction; Inert atmosphere;

DOI:10.3390/molecules201219789

Reference yield: 15.0%

7-hydroxy-4-methyl-2-oxo-2H-1-benzopyran tetrabutylammonium salt (84380-11-0) + 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride (4451-36-9) → 4′-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside (67945-53-3)

Guidance literature:

In acetonitrile; at 20 ℃; for 72h; Inert atmosphere;

DOI:10.1039/c9ob02540e

Reference yield: 98.0%

4′-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside (67945-53-3) → 4-methyl-umbelliferyl α-D-glucopyranoside (17833-43-1,39940-54-0)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 3h; pH=10; Inert atmosphere;

DOI:10.1039/c9ob02540e

upstream raw materials:

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

β-D-glucose pentaacetate

7-hydroxy-4-methyl-2-oxo-2H-1-benzopyran tetrabutylammonium salt

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride

Downstream raw materials:

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

4-methyl-umbelliferyl α-D-glucopyranoside