4-Methylumbelliferyl alpha-L-arabinopyranoside

Base Information

• Chemical Name: 4-Methylumbelliferyl alpha-L-arabinopyranoside
• CAS No.: 69414-26-2
• Molecular Formula: C₁₅H₁₆O₇
• Molecular Weight: 308.288
• Hs Code.: 2934999090
• European Community (EC) Number: 273-991-2
• DSSTox Substance ID: DTXSID101266395
• Nikkaji Number: J317.982F
• Wikidata: Q27162339
• Mol file: 69414-26-2.mol

Synonyms:69414-26-2;4-Methylumbelliferyl alpha-L-arabinopyranoside;4-Methylumbelliferyl a-L-arabinopyranoside;4-methylumbelliferyl-alpha-l-arabinopyranoside;4-methylumbelliferyl alpha-l-arabinoside;2H-1-Benzopyran-2-one,7-(a-L-arabinopyranosyloxy)-4-methyl-;4-Methylumbelliferyl I+/--L-arabinopyranoside;4-methyl-7-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxychromen-2-one;4-MU-a-L-Ara;4-Methylumbelliferyla-L-arabinopyranoside;SCHEMBL4609785;CHEBI:90130;DTXSID101266395;AMY41680;MFCD00064087;BS-43832;4-Methylumbelliferyl |A-L-arabinopyranoside;NS00090896;4-Methylumbelliferyl alpha -L-arabinopyranoside;T72837;Q27162339;4-methyl-2-oxo-2H-1-benzopyran-7-yl alpha-L-arabinopyranoside;4-methyl-7-((2S,3R,4S,5S)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yloxy)-2H-chromen-2-one;4-METHYL-7-{[(2S,3R,4S,5S)-3,4,5-TRIHYDROXYOXAN-2-YL]OXY}CHROMEN-2-ONE

Chemical Property of 4-Methylumbelliferyl alpha-L-arabinopyranoside

Chemical Property:

• Appearance/Colour: WHITE POWDER
• Vapor Pressure: 6.29E-14mmHg at 25°C
• Boiling Point: 572.1 ºC at 760 mmHg
• Flash Point: 217.3 ºC
• PSA: 109.36000
• Density: 1.514 g/cm³
• LogP: -0.08080
• Storage Temp.: −20°C
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 308.08960285
• Heavy Atom Count: 22
• Complexity: 463

Purity/Quality:

98%, ^*data from raw suppliers

4-Methylumbelliferyl a-L-arabinopyranoside ^*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: CC1=CC(=O)OC2=C1C=CC(=C2)OC3C(C(C(CO3)O)O)O
• Isomeric SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)O[C@H]3[C@@H]([C@H]([C@H](CO3)O)O)O
• Uses: 4-Methylumbelliferyl alpha-L-arabinopyranoside is a derivative of arabinopyranose.

Technology Process of 4-Methylumbelliferyl alpha-L-arabinopyranoside

There total 16 articles about 4-Methylumbelliferyl alpha-L-arabinopyranoside 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: 96.0%

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) + α-D-xylopyranosyl fluoride (3945-26-4,4536-02-1,4556-49-4,4556-50-7,16051-71-1,22893-62-5,90822-01-8,108393-17-5) → 4-methylumbelliferyl-α-D-xylopyranoside (65502-34-3,69414-26-2)

Guidance literature:

With α-thioglycoligase YicI-D482A mutant; In aq. phosphate buffer; at 25 ℃; for 4h; pH=8.0; pH-value; Enzymatic reaction;

DOI:10.1016/j.molcatb.2012.10.008

Reference yield: 79.0%

4′-methylumbelliferyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside (6734-34-5) → 4-methylumbellifer-7-yl β-D-xylopyranoside (6734-33-4,65502-34-3,69414-26-2)

Guidance literature:

With potassium hydroxide; In methanol; at 20 ℃; for 0.416667h;

DOI:10.3390/molecules201219789

Reference yield: 60.0%

C21H22O10 → 4-Methylumbelliferyl-β-D-ribopyranosid (66912-32-1,65502-34-3,69414-26-2)

Guidance literature:

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

DOI:10.1021/jm200983e

upstream raw materials:

4′-methylumbelliferyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside

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

p-nitrophenyl β-D-xylopyranoside

1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose

Downstream raw materials:

4-methylumbelliferyl β-D-xylopyranosyl-(1->4)-β-D-xylopyranoside

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、 -. "CARBONIC ANHYDRASE INHIBITORS WITH ANTIMETASTATIC ACTIVITY". Page/Page column 22-29. . Retrieved 2012/06/15.