3,4,6-Tri-O-benzoyl-2,5-anhydro-D-allonic acid

Base Information

• Chemical Name: 3,4,6-Tri-O-benzoyl-2,5-anhydro-D-allonic acid
• CAS No.: 23316-68-9
• Molecular Formula: C₂₇H₂₂O₉
• Molecular Weight: 490.466
• DSSTox Substance ID: DTXSID101243018
• Nikkaji Number: J1.232.452I
• Mol file: 23316-68-9.mol

Synonyms:SCHEMBL2418301;SKHMDDZYUHLTKM-SSGKUCQKSA-N;DTXSID101243018;3,4,6-Tri-O-benzoyl-2,5-anhydro-D-allonic acid;D-Allonic acid, 2,5-anhydro-, 3,4,6-tribenzoate;2,5-Anhydro-3-O,4-O,6-O-tribenzoyl-D-allonic acid;23316-68-9

Chemical Property of 3,4,6-Tri-O-benzoyl-2,5-anhydro-D-allonic acid

Chemical Property:

• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 11
• Exact Mass: 490.12638228
• Heavy Atom Count: 36
• Complexity: 778

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)OCC2C(C(C(O2)C(=O)O)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)C(=O)O)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4

Technology Process of 3,4,6-Tri-O-benzoyl-2,5-anhydro-D-allonic acid

There total 4 articles about 3,4,6-Tri-O-benzoyl-2,5-anhydro-D-allonic acid 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: 82.0%

2,3,5-tri-O-benzoyl-β-D-ribofuranosyl-1-carbonitrile (23316-67-8) → (2R,3R,4R,5R)-3,4-bis(benzoyloxy)-5-((benzoyloxy)methyl)tetrahydrofuran-2-carboxylic acid (23316-68-9)

Guidance literature:

With hydrogenchloride; water; In acetic acid; at 100 ℃; for 0.25h;

DOI:10.1039/a905177e

Reference yield:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) → (2R,3R,4R,5R)-3,4-bis(benzoyloxy)-5-((benzoyloxy)methyl)tetrahydrofuran-2-carboxylic acid (23316-68-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / SnCl₄ / 1,2-dichloro-ethane / 0.03 h

2: 82 percent / HCl; H₂O / acetic acid / 0.25 h / 100 °C

With hydrogenchloride; water; tin(IV) chloride; In acetic acid; 1,2-dichloro-ethane; 1: Substitution / 2: Hydrolysis;

DOI:10.1039/a905177e

Reference yield:

C28H26O8 → (2R,3R,4R,5R)-3,4-bis(benzoyloxy)-5-((benzoyloxy)methyl)tetrahydrofuran-2-carboxylic acid (23316-68-9)

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate / dichloromethane / 4 h / 20 °C

2: hydrogenchloride / water / 0.25 h / 80 °C

With hydrogenchloride; boron trifluoride diethyl etherate; In dichloromethane; water;

DOI:10.1039/c9cc07184a

upstream raw materials:

2,3,5-tri-O-benzoyl-β-D-ribofuranosyl-1-carbonitrile

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Downstream raw materials:

(1S)-tri-O-benzoyl-1-[1,2,4]triazolo[3,4-a]phthalazin-3-yl-D-1,4-anhydro-ribitol

N-2-pyridilmethyl-2,5-anhydro-3,4,6-tri-O-benzoyl-D-allonamide

(4S,trans)-4-benzoyloxy-5-benzoyloxymethyl-4,5-dihydrofuran-N-(2-pyridylmethyl)furan-2-carboxamide

C₃₁H₂₅ClN₄O₈