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

Base Information

• Chemical Name: 4-Methylumbelliferyl2,3,4,6-tetra-O-acetyl-a-D-mannopyranoside
• CAS No.: 28541-71-1
• Molecular Formula: C24H26 O12
• Molecular Weight: 506.463
• Mol file: 28541-71-1.mol

Synonyms:Mannopyranoside,4-methyl-2-oxo-2H-1-benzopyran-7-yl, tetraacetate, a-D- (8CI); 4-Methylumbelliferyl tetra-O-acetyl-a-D-mannopyranoside

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

Chemical Property:

• Melting Point: 221-223°C
• PSA: 153.87000
• LogP: 1.56330

Purity/Quality:

98% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A protected substrate for mannosidase.

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

There total 2 articles about 4-Methylumbelliferyl2,3,4,6-tetra-O-acetyl-a-D-mannopyranoside 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: 62.0%

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) + β-D-mannopyranose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) → 4′-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (28541-71-1) + 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: 48.0%

sodium 4-methylumbelliferonate (5980-33-6) + 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride (572-10-1,4451-35-8,4451-36-9,14227-52-2,14227-87-3,14227-88-4,14257-40-0,17081-03-7,19186-60-8,57237-01-1,65982-17-4,65982-18-5,65982-19-6,66966-08-3,144299-57-0) → 4′-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (28541-71-1)

Guidance literature:

In N,N,N,N,N,N-hexamethylphosphoric triamide; at 20 ℃; for 58h;

DOI:10.1021/ol062889f

Reference yield: 100.0%

4′-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (28541-71-1) → 4-methylumbellifer-7-yl α-D-mannopyranoside (28541-83-5,39940-54-0)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 0.5h;

DOI:10.1021/jm200983e

upstream raw materials:

sodium 4-methylumbelliferonate

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride

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

β-D-mannopyranose pentaacetate

Downstream raw materials:

4-methylumbellifer-7-yl α-D-mannopyranoside