4-Methylumbelliferyl alpha-L-arabinofuranoside

Base Information

• Chemical Name: 4-Methylumbelliferyl alpha-L-arabinofuranoside
• CAS No.: 77471-44-4
• Molecular Formula: C₁₅H₁₆O₇
• Molecular Weight: 308.288
• Hs Code.: 29400090
• DSSTox Substance ID: DTXSID201265871
• Nikkaji Number: J928.973I
• Mol file: 77471-44-4.mol

Synonyms:77471-44-4;4-Methylumbelliferyl alpha-L-arabinofuranoside;4-Methylumbelliferyl |A-L-arabinofuranoside;7-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4-methylchromen-2-one;2H-1-Benzopyran-2-one,7-(a-L-arabinofuranosyloxy)-4-methyl-;7-(((2S,3R,4R,5S)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-4-methyl-2H-chromen-2-one;4-methylumbelliferyl-alpha-l-arabinofuranoside;4-Methylumbelliferyl a-L-arabinofuranoside;SCHEMBL366087;4-METHYLUMBELLIFERYL ALPHA-L-ARABINOSFURANOSIDE;DTXSID201265871;7-{[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-4-methyl-2H-chromen-2-one;MFCD00057308;4-Methylumbelliferyl-alpha-L-arabinoside;4-Methylumbelliferyl ?-L-Arabinosfuranoside;HY-137490;CS-0139311;4-Methylumbelliferyl alpha -L-arabinofuranoside;G77031;7-((2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yloxy)-4-methyl-2H-chromen-2-one

Chemical Property of 4-Methylumbelliferyl alpha-L-arabinofuranoside

Chemical Property:

• Vapor Pressure: 3.24E-15mmHg at 25°C
• Refractive Index: 1.631
• Boiling Point: 599.4 °C at 760 mmHg
• Flash Point: 228.1 °C
• Density: 1.486 g/cm³
• Storage Temp.: −20°C
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 308.08960285
• Heavy Atom Count: 22
• Complexity: 463

Purity/Quality:

98% ^*data from raw suppliers

4-Methylumbelliferyl a-L-arabinofuranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 20/22-36/38-39/23/24/25-23/24/25-11
• Safety Statements: 7-24-45-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)OC3C(C(C(O3)CO)O)O
• Isomeric SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H](O3)CO)O)O
• Uses: 4-Methylumbelliferyl α-L-Arabinosfuranoside (cas# 77471-44-4) is a compound useful in organic synthesis.

Technology Process of 4-Methylumbelliferyl alpha-L-arabinofuranoside

There total 7 articles about 4-Methylumbelliferyl alpha-L-arabinofuranoside 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: 10.0%

4-methylumbelliferyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranoside (106488-03-3,113728-14-6,195385-92-3) → 7-hydroxy-4-methylcoumarin-7-yl α-L-arabinofuranoside (77471-44-4,195385-93-4)

Guidance literature:

With ammonia; In methanol; at 4 ℃; for 72h;

DOI:10.1016/0008-6215(88)84045-X

Reference yield:

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) → 7-hydroxy-4-methylcoumarin-7-yl α-L-arabinofuranoside (77471-44-4,195385-93-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / p-TsOH / toluene / 3 h / Heating

2: 90 percent / 0.5 M NaOMe/MeOH / 2 h / Ambient temperature

3: 1.) 0.05 M aq. NaIO₄, 2.) NaBH₄ / 1.) 20 min, 2.) RT, 2 h

With methanol; sodium tetrahydroborate; sodium periodate; sodium methylate; toluene-4-sulfonic acid; In toluene;

DOI:10.1016/0008-6215(95)00239-P

Reference yield:

7-hydroxy-4-methyl-2-oxo-2H-1-benzopyran tetrabutylammonium salt (84380-11-0) → 7-hydroxy-4-methylcoumarin-7-yl α-L-arabinofuranoside (77471-44-4,195385-93-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / SnCl₄ / CH₂Cl₂ / 6 h / Ambient temperature

2: 90 percent / 0.5 M NaOMe/MeOH / 2 h / Ambient temperature

3: 1.) 0.05 M aq. NaIO₄, 2.) NaBH₄ / 1.) 20 min, 2.) RT, 2 h

With methanol; sodium tetrahydroborate; sodium periodate; sodium methylate; tin(IV) chloride; In dichloromethane;

DOI:10.1016/0008-6215(95)00239-P

upstream raw materials:

4-methylumbelliferyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranoside

β-7-hydroxy-4-methylcoumarin-7-yl D-galactofuranoside

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

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

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