4-Methylumbelliferyl2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside

Base Information

• Chemical Name: 4-Methylumbelliferyl2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside
• CAS No.: 124167-45-9
• Molecular Formula: C₂₄H₂₇NO₁₁
• Molecular Weight: 505.478
• Mol file: 124167-45-9.mol

Synonyms:4-Methylumbelliferyl2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside

Chemical Property of 4-Methylumbelliferyl2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside

Chemical Property:

• Boiling Point: 699.0±55.0 °C(Predicted)
• PKA: 13.40±0.70(Predicted)
• PSA: 156.67000
• Density: 1.36±0.1 g/cm3(Predicted)
• LogP: 1.52720

Purity/Quality:

98% ^*data from raw suppliers

4-Methylumbelliferyl2-Acetamido-2-deoxy-3,4,6-tri-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-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-Glucopyranoside (cas# 124167-45-9) is a compound useful in organic synthesis.

Technology Process of 4-Methylumbelliferyl2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside

There total 6 articles about 4-Methylumbelliferyl2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-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:

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) + (3R,4R,5R,6R)-3-acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate (76375-60-5) → 4-methylumbelliferyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranoside (124167-45-9)

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate); In 1,2-dichloro-ethane; at 130 ℃; for 0.416667h; stereoselective reaction; Microwave irradiation;

DOI:10.1021/acssynbio.9b00168

Reference yield:

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) → 4-methylumbelliferyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranoside (124167-45-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 33 percent / silver trifluoromethanesulfonate, sym-collidine, 4 Angstroem molecular sieves / CH₂Cl₂ / Ambient temperature

2: 1.) H₂; / 1.) 5percent palladium-on charcoal / 1.) aq. EtOH, 2h; 2.) pyridine, 1h, room temperature

With 2,4,6-trimethyl-pyridine; 4 A molecular sieve; hydrogen; silver trifluoromethanesulfonate; palladium on activated charcoal; In dichloromethane;

Reference yield:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride (67817-37-2) → 4-methylumbelliferyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranoside (124167-45-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 33 percent / silver trifluoromethanesulfonate, sym-collidine, 4 Angstroem molecular sieves / CH₂Cl₂ / Ambient temperature

2: 1.) H₂; / 1.) 5percent palladium-on charcoal / 1.) aq. EtOH, 2h; 2.) pyridine, 1h, room temperature

With 2,4,6-trimethyl-pyridine; 4 A molecular sieve; hydrogen; silver trifluoromethanesulfonate; palladium on activated charcoal; In dichloromethane;

upstream raw materials:

acetic anhydride

4-methylumbelliferyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranoside

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

3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride

Downstream raw materials:

4-methylumbelliferyl 2-acetamido-2-deoxy-α-D-galactopyranoside

Refernces

• 1、 Szweda, R.,Spohr, U.,Lemieux, R. U.,Schindler, D.,Bishop, D. F.,Desnick, R. J.. "Synthesis of 4-methylumbelliferyl glycosides for the detection of α- and β-D-galactopyranosaminidases". . p. 1388 - 1391. Retrieved 2007/10/02.