4-Methylumbelliferyl beta-L-fucopyranoside

Base Information

• Chemical Name: 4-Methylumbelliferyl beta-L-fucopyranoside
• CAS No.: 72601-82-2
• Molecular Formula: C₁₆H₁₈O₇
• Molecular Weight: 322.315
• Hs Code.: 29400090
• European Community (EC) Number: 276-730-0
• DSSTox Substance ID: DTXSID001159222
• Nikkaji Number: J296.329I
• Mol file: 72601-82-2.mol

Synonyms:72601-82-2;4-Methylumbelliferyl beta-L-fucopyranoside;4-Methylumbelliferyl beta-L-fucoside;EINECS 276-730-0;4-methyl-7-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-2-one;7-[(6-deoxy-beta-L-galactopyranosyl)oxy]-4-methyl-2H-1-benzopyran-2-one;C16H18O7;7-((6-Deoxy-beta-L-galactopyranosyl)oxy)-4-methyl-2H-1-benzopyran-2-one;4-Methylumbelliferyl-beta-L-fucopyranoside;C16-H18-O7;MFCD00067660;SCHEMBL2540609;DTXSID001159222;AMY41688;4-Methylumbelliferyl beta -L-fucoside;AKOS016015748;4-Methylumbelliferyl I(2)-L-fucopyranoside;4-Methyl-7-(beta-L-fucopyranosyloxy)-2H-1-benzopyran-2-one;2H-1-Benzopyran-2-one,7-[(6-deoxy-b-L-galactopyranosyl)oxy]-4-methyl-;4-Methyl-7-(((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2H-chromen-2-one;4-methyl-7-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)-2H-chromen-2-one;4-Methyl-7-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-2-one;4-methyl-7-{[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2H-chromen-2-one

Chemical Property of 4-Methylumbelliferyl beta-L-fucopyranoside

Chemical Property:

• Appearance/Colour: White to off-white crystalline powder
• Vapor Pressure: 1.21E-13mmHg at 25°C
• Melting Point: 221-225°C
• Refractive Index: 1.621
• Boiling Point: 565.9 °C at 760 mmHg
• Flash Point: 211.3 °C
• PSA: 109.36000
• Density: 1.441 g/cm³
• LogP: 0.30770
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 322.10525291
• Heavy Atom Count: 23
• Complexity: 491

Purity/Quality:

98% ^*data from raw suppliers

4-Methylumbelliferyl b-L-fucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2=CC3=C(C=C2)C(=CC(=O)O3)C)O)O)O
• Isomeric SMILES: C[C@H]1[C@H]([C@H]([C@@H]([C@H](O1)OC2=CC3=C(C=C2)C(=CC(=O)O3)C)O)O)O

Technology Process of 4-Methylumbelliferyl beta-L-fucopyranoside

There total 8 articles about 4-Methylumbelliferyl beta-L-fucopyranoside 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: 69.0%

acetic acid 4,5-diacetoxy-6-methyl-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-3-yl ester → 4-methylumbelliferyl-β-L-fucopyranoside (54322-38-2,55487-93-9,72601-82-2)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 1h;

DOI:10.1021/ol062889f

Reference yield: 58.0%

C22H24O10 (106488-00-0) → 4-methylumbellifer-7-yl α-L-rhamnopyranoside (106488-05-5,54322-38-2,55487-93-9,72601-82-2)

Guidance literature:

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

DOI:10.1021/jm200983e

Reference yield:

1,2,3,4-tetra-O-acetyl-L-rhamnopyranose (7404-35-5,17081-04-8,20853-37-6,24332-95-4,27821-10-9,27821-11-0,33947-15-8,34371-40-9,34371-41-0,35521-79-0,36807-81-5,36807-82-6,50615-78-6,51921-33-6,62182-03-0,64913-16-2,70004-81-8,84622-47-9,87303-56-8,108942-32-1,108942-33-2,109430-94-6,143394-72-3,30021-94-4) → 4-methylumbellifer-7-yl α-L-rhamnopyranoside (106488-05-5,54322-38-2,55487-93-9,72601-82-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: morpholine / dichloromethane / 20 °C / Inert atmosphere

2.1: dichloromethane / 1 h / 0 °C / Inert atmosphere

2.2: 0.5 h / 0 °C / Inert atmosphere

3.1: boron trifluoride dimethyl etherate / dichloromethane / 20 °C / Inert atmosphere

4.1: methanol; sodium methylate / 0.5 h / 20 °C

With morpholine; methanol; boron trifluoride dimethyl etherate; sodium methylate; In dichloromethane;

DOI:10.1021/jm200983e

upstream raw materials:

2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide

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

C₂₂H₂₄O₁₀

1,2,3,4-tetra-O-acetyl-L-rhamnopyranose

Refernces

• 1、 Touisni, Nadia,Maresca, Alfonso,McDonald, Paul C.,Lou, Yuanmei,Scozzafava, Andrea,Dedhar, Shoukat,Winum, Jean-Yves,Supuran, Claudiu T.. "Glycosyl coumarin carbonic anhydrase IX and XII inhibitors strongly attenuate the growth of primary breast tumors". experimental part. p. 8271 - 8277. Retrieved 2012/02/06.