4-METHYLUMBELLIFERYL-alpha-D-MANNOPYRANOSIDE

Base Information

• Chemical Name: 4-METHYLUMBELLIFERYL-alpha-D-MANNOPYRANOSIDE
• CAS No.: 28541-83-5
• Molecular Formula: C16H18O8
• Molecular Weight: 338.314
• Hs Code.: 29400090
• European Community (EC) Number: 249-073-2
• DSSTox Substance ID: DTXSID001020647
• Nikkaji Number: J250.732C
• Pharos Ligand ID: QKMNQFB3KA11
• ChEMBL ID: CHEMBL1172750
• Mol file: 28541-83-5.mol

Synonyms:4-methylumbelliferyl-beta-D-mannoside;4-methylumbelliferylmannoside;4-MUAMPD;methylumbelliferyl-alpha-D-mannopyranoside;MU-B-Man;para-methylumbelliferyl-alpha-D-mannopyranoside

Chemical Property of 4-METHYLUMBELLIFERYL-alpha-D-MANNOPYRANOSIDE

Chemical Property:

• Appearance/Colour: White Solid
• Melting Point: 190 °C
• Boiling Point: 626.9 °C at 760 mmHg
• Flash Point: 233.9 °C
• PSA: 129.59000
• Density: 1.522 g/cm³
• LogP: -0.71990
• Storage Temp.: 2-8°C
• Solubility.: pyridine: 20 mg/mL, clear, faintly yellow
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 338.10016753
• Heavy Atom Count: 24
• Complexity: 506

Purity/Quality:

98%, ^*data from raw suppliers

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

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Canonical SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)OC3C(C(C(C(O3)CO)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)O)O
• Uses: A substrate for mannosidase. N-acetyl a-D-glucosaminidase substrate A substrate for mannosidase. Has use as an analytical reagent for studying biomass degradation by fungi.

Technology Process of 4-METHYLUMBELLIFERYL-alpha-D-MANNOPYRANOSIDE

There total 9 articles about 4-METHYLUMBELLIFERYL-alpha-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: 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

Reference yield:

sodium 4-methylumbelliferonate (5980-33-6) → 4-methylumbellifer-7-yl α-D-mannopyranoside (28541-83-5,39940-54-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 48 percent / hexamethylphosphoric acid triamide / 58 h / 20 °C

2: 70 percent / NaOMe; MeOH / 1 h / 20 °C

With methanol; sodium methylate; In N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1021/ol062889f

Reference yield:

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-methylumbellifer-7-yl α-D-mannopyranoside (28541-83-5,39940-54-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 48 percent / hexamethylphosphoric acid triamide / 58 h / 20 °C

2: 70 percent / NaOMe; MeOH / 1 h / 20 °C

With methanol; sodium methylate; In N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1021/ol062889f

upstream raw materials:

4′-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

sodium 4-methylumbelliferonate

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

D-Mannose pentaacetate

Refernces

• 1、 Wei, Xianhu,Ma, Yanxia,Wu, Qingping,Zhang, Jumei,Cai, Zhihe,Lu, Mianfei,Ferro, Vito. "An improved helferich method for the α/β-stereoselective synthesis of 4-methylumbelliferyl glycosides for the detection of microorganisms". . p. 21681 - 21699. Retrieved 2016/01/25.
• 2、 -. "COMPOUNDS AND METHODS FOR TREATING BACTERIAL INFECTIONS". Page/Page column 69, 72. . Retrieved 2011/05/06.