1,2,3,5-Tetra-O-acetyl-alpha-L-arabinofuranose

Base Information

• Chemical Name: 1,2,3,5-Tetra-O-acetyl-alpha-L-arabinofuranose
• CAS No.: 79120-81-3
• Molecular Formula: C₁₃H₁₈O₉
• Molecular Weight: 318.281
• European Community (EC) Number: 623-306-1
• Nikkaji Number: J1.839.106F
• Mol file: 79120-81-3.mol

Synonyms:79120-81-3;1,2,3,5-Tetra-O-acetyl-alpha-L-arabinofuranose;AKOS015913518;[(2S,3S,4R,5S)-3,4,5-triacetyloxyoxolan-2-yl]methyl acetate;(2S,3R,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate

Chemical Property of 1,2,3,5-Tetra-O-acetyl-alpha-L-arabinofuranose

Chemical Property:

• Vapor Pressure: 3.76E-06mmHg at 25°C
• Boiling Point: 385.6°C at 760 mmHg
• Flash Point: 168.5°C
• PSA: 114.43000
• Density: 1.29g/cm³
• LogP: -0.29910
• Storage Temp.: 2-8°C
• 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:

98% ^*data from raw suppliers

1,2,3,5-Tetra-O-acetyl-L-arabinofuranose ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37

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@@H](O1)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of 1,2,3,5-Tetra-O-acetyl-alpha-L-arabinofuranose

There total 44 articles about 1,2,3,5-Tetra-O-acetyl-alpha-L-arabinofuranose 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:

L-(+)-arabinose

acetic anhydride

L-arabinose

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

Downstream raw materials:

Acetic acid (2S,3R,4S,5S)-4-acetoxy-5-acetoxymethyl-2-(4-methoxy-phenoxy)-tetrahydro-furan-3-yl ester

p-cresyl 2-O-benzyl-3,5-O-(di-tert-butylsilylene)-1-thio-α-L-arabinofuranoside

4'-methylphenyl 1-thio-α-L-arabinofuranoside

4'-methoxyphenyl α-L-arabinofuranoside

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