D-Arabinofuranose, 1,2,3,5-tetraacetate

Base Information

• Chemical Name: D-Arabinofuranose, 1,2,3,5-tetraacetate
• CAS No.: 61826-42-4
• Molecular Formula: C13H18O9
• Molecular Weight: 318.281
• DSSTox Substance ID: DTXSID201278464
• Nikkaji Number: J1.103.645G
• Mol file: 61826-42-4.mol

Synonyms:61826-42-4;SCHEMBL7040813;DTXSID201278464;D-Arabinofuranose, 1,2,3,5-tetraacetate

Chemical Property of D-Arabinofuranose, 1,2,3,5-tetraacetate

Chemical Property:

• Boiling Point: 385.6±42.0 °C(Predicted)
• PSA: 71.06000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: 0.79880
• 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:

97% ^*data from raw 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

Technology Process of D-Arabinofuranose, 1,2,3,5-tetraacetate

There total 45 articles about D-Arabinofuranose, 1,2,3,5-tetraacetate 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:

L-(+)-arabinose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) + acetic anhydride (108-24-7) → 1,2,3,6-tetra-O-acetyl-5-deoxy-α-L-arabino-hexofuranose (13035-61-5,23094-61-3,28708-32-9,39727-26-9,42927-46-8,43225-70-3,50730-26-2,56272-01-6,61248-15-5,61826-42-4,61849-90-9,69855-18-1,69855-19-2,79120-80-2,79120-81-3,86782-36-7,86782-94-7,105453-36-9,144490-03-9) + 1,2,3,6-tetra-O-acetyl-5-deoxy-β-L-arabino-hexofuranose (13035-61-5,23094-61-3,28708-32-9,39727-26-9,42927-46-8,43225-70-3,50730-26-2,56272-01-6,61248-15-5,61826-42-4,61849-90-9,69855-18-1,69855-19-2,79120-80-2,79120-81-3,86782-36-7,86782-94-7,105453-36-9,144490-03-9) + 1,2,3,4-tetra-O-acetyl-β-L-arabinopyranose (4258-00-8) + 1,2,3,4-tetra-O-acetyl-α-L-arabinopyranose (1233-03-0,2595-11-1,4026-34-0,4049-33-6,4049-34-7,4257-95-8,4257-98-1,4258-00-8,4627-30-9,17080-99-8,19186-37-9,25227-11-6,25243-38-3,62446-93-9,62929-49-1,67226-03-3,78087-60-2,78088-17-2,82890-16-2,86782-34-5,86782-35-6,92218-63-8,99880-95-2,108646-05-5,115939-79-2,123163-97-3,142130-89-0)

Guidance literature:

With pyridine; at 0 ℃; Yield given. Yields of byproduct given;

Reference yield:

L-(+)-arabinose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) + acetic anhydride (108-24-7) → 1,2,3,6-tetra-O-acetyl-5-deoxy-α-L-arabino-hexofuranose (13035-61-5,23094-61-3,28708-32-9,39727-26-9,42927-46-8,43225-70-3,50730-26-2,56272-01-6,61248-15-5,61826-42-4,61849-90-9,69855-18-1,69855-19-2,79120-80-2,79120-81-3,86782-36-7,86782-94-7,105453-36-9,144490-03-9) + 1,2,3,6-tetra-O-acetyl-5-deoxy-β-L-arabino-hexofuranose (13035-61-5,23094-61-3,28708-32-9,39727-26-9,42927-46-8,43225-70-3,50730-26-2,56272-01-6,61248-15-5,61826-42-4,61849-90-9,69855-18-1,69855-19-2,79120-80-2,79120-81-3,86782-36-7,86782-94-7,105453-36-9,144490-03-9) + 1,2,3,4-tetra-O-acetyl-β-L-arabinopyranose (4258-00-8) + 1,2,3,4-tetra-O-acetyl-α-L-arabinopyranose (1233-03-0,2595-11-1,4026-34-0,4049-33-6,4049-34-7,4257-95-8,4257-98-1,4258-00-8,4627-30-9,17080-99-8,19186-37-9,25227-11-6,25243-38-3,62446-93-9,62929-49-1,67226-03-3,78087-60-2,78088-17-2,82890-16-2,86782-34-5,86782-35-6,92218-63-8,99880-95-2,108646-05-5,115939-79-2,123163-97-3,142130-89-0)

Guidance literature:

With pyridine; at 0 ℃; Yield given. Yields of byproduct given;

upstream raw materials:

D-Arabinose

acetic anhydride

L-(+)-arabinose

L-arabinose

Downstream raw materials:

7-α-D-Arabinofuranosyl theophylline

1-(p-thiocresyl)-2,3,5-tri-O-acetyl-α-D-arabinofuranoside

N²-acetyl-9-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)-O⁶-diphenylcarbamoylguanine

1-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)thymine