(3R,4R,5R)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate

Base Information

• Chemical Name: (3R,4R,5R)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate
• CAS No.: 28708-32-9
• Molecular Formula: C13H18O9
• Molecular Weight: 318.281
• Hs Code.: 2932999099
• European Community (EC) Number: 249-174-1
• DSSTox Substance ID: DTXSID401289952
• Nikkaji Number: J250.766H
• Mol file: 28708-32-9.mol

Synonyms:28708-32-9;(3R,4R,5R)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate;D-Ribofuranose, tetraacetate;Tetra-O-acetyl-D-ribofuranose;EINECS 249-174-1;Tetraacetylribofuranose;D-Ribofuranose, 1,2,3,5-tetraacetate;[(2R,3R,4R)-3,4,5-triacetyloxyoxolan-2-yl]methyl acetate;C13H18O9;1,2,3,5-Tetra-O-acetyl-D-ribofuranose;C13-H18-O9;tetra-O-acetylribofuranose;d-ribofuranose tetraacetate;SCHEMBL258821;Ribofuranose, tetraacetate, D-;IHNHAHWGVLXCCI-PFGBXZAXSA-N;DTXSID401289952;(3R,4R,5R)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyltriacetate;MFCD03788309;AKOS008901402;AKOS015896916;D-Ribofuranose,1,2,3,5-tetraacetate;1,2,3,5-tetra-O-acetyl-ribofuranose;CS-W005013;DS-5390;E82977;A876658

Chemical Property of (3R,4R,5R)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 82 °C(Solv: chloroform (67-66-3))
• Refractive Index: 1.475
• Boiling Point: 385.624 °C at 760 mmHg
• Flash Point: 168.471 °C
• PSA: 114.43000
• Density: 1.29 g/cm³
• LogP: -0.29910
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 318.09508215
• Heavy Atom Count: 22
• Complexity: 458

Purity/Quality:

99% ^*data from raw suppliers

(3R,4R,5R)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyltriacetate 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(O1)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@H](C(O1)OC(=O)C)OC(=O)C)OC(=O)C
• Uses: Tetra-O-acetyl-D-ribofuranose is a useful product for proteomic research.

Technology Process of (3R,4R,5R)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate

There total 52 articles about (3R,4R,5R)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate 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%

acetic anhydride (108-24-7) + methyl 2,3,5-tri-O-acetyl-α,β-D-arabinofuranoside (90244-44-3,110415-62-8) → 1,2,3,5-tetra-O-acetyl-α-D-arabinofuranose (13035-61-5,23094-61-3,28708-32-9,39727-26-9,42927-46-8,50730-26-2,56272-01-6,61248-15-5,61826-42-4,61849-90-9,69855-18-1,69855-19-2,79120-80-2,79120-81-3,86782-36-7,86782-94-7,105453-36-9,144490-03-9,43225-70-3)

Guidance literature:

With sulfuric acid; In acetic acid;

DOI:10.3987/COM-08-S(F)59

Reference yield: 99.0%

D-Ribose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) + acetic anhydride (108-24-7) → 1,2,3,5-tetra-O-acetyl-D-ribofuranose (28708-32-9)

Guidance literature:

With pyridine; at 80 ℃;

DOI:10.1016/j.tetlet.2008.05.076

Reference yield:

(2R,3R,4R)-2-(acetoxymethyl)-5-methoxytetrahydrofuran-3,4-diyl diacetate (52554-28-6,110415-62-8) + acetic anhydride (108-24-7) → 1,2,3,5-tetra-O-acetyl-D-ribofuranose (28708-32-9)

Guidance literature:

With sulfuric acid; In acetic acid; at 20 ℃; for 3h;

DOI:10.1016/j.bmcl.2008.03.033

upstream raw materials:

L-(+)-arabinose

acetic anhydride

L-arabinose

methyl 2,3,6-tri-O-acetyl-5-deoxy-L-arabino-hexofuranoside

Downstream raw materials:

1-β-D-ribofuranosylpyridin-4-one-3-carboxamide

2-chloro-4-nitrophenyl 2,3,5-tri-O-acetyl-α-L-arabinofuranoside

2,3,5-tri-O-acetyl-1-O-(4-phenylphenyl)-β-D-ribofuranoside

2,3,5-tri-O-acetyl-1-O-(4-phenylphenyl)-α-D-ribofuranoside

Refernces

• 1、 Ichikawa, Satoshi,Katsuyama, Akira,Kitahata, Shun. "A Synthesis Strategy for the Production of a Macrolactone of Gulmirecin A via a Ni(0)-Mediated Reductive Cyclization Reaction". supporting information. . Retrieved 2020/03/30.
• 2、 Fan, Zhanfang,Guo, Chun,Hou, Zhuang,Li, Chuanchao,Lin, Bin,Liu, Yang,Liu, Yichuang,Wang, Yitong,Zhang, Miao. "Design, synthesis and biological evaluation of carbohydrate-based sulphonamide derivatives as topical antiglaucoma agents through selective inhibition of carbonic anhydrase II". . p. 383 - 390. Retrieved 2019/12/30.