D-arabino-Hex-1-enitol, 2,6-anhydro-1-deoxy-, tribenzoate

Base Information

• Chemical Name: D-arabino-Hex-1-enitol, 2,6-anhydro-1-deoxy-, tribenzoate
• CAS No.: 18524-09-9
• Molecular Formula: C₂₇H₂₂O₇
• Molecular Weight: 458.467
• DSSTox Substance ID: DTXSID601198240
• Mol file: 18524-09-9.mol

Synonyms:D-arabino-Hex-1-enitol, 2,6-anhydro-1-deoxy-, tribenzoate;DTXSID601198240;18524-09-9

Chemical Property of D-arabino-Hex-1-enitol, 2,6-anhydro-1-deoxy-, tribenzoate

Chemical Property:

• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 458.13655304
• Heavy Atom Count: 34
• Complexity: 729

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=C1C(C(C(CO1)OC(=O)C2=CC=CC=C2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4

Technology Process of D-arabino-Hex-1-enitol, 2,6-anhydro-1-deoxy-, tribenzoate

There total 8 articles about D-arabino-Hex-1-enitol, 2,6-anhydro-1-deoxy-, tribenzoate 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: 72.0%

1,5-anhydro-2,3,4-tri-O-benzoyl-6-deoxy-6-iodo-D-mannitol (119645-59-9) → 1,5-anhydro-2,3,4-tri-O-benzoyl-6-deoxy-D-lyxo-hex-5-enitol (18524-09-9)

Guidance literature:

With pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; at 40 ℃; for 16h;

DOI:10.1016/0008-6215(88)84027-8

Reference yield: 11.0%

1,3,4,5-tetra-O-benzoyl-β-D-fructopyranosyl bromide (17187-64-3) → 1,5-anhydro-2,3,4-tri-O-benzoyl-6-deoxy-D-lyxo-hex-5-enitol (18524-09-9) + Tri-O-benzoyl-endo-D-fructal

Guidance literature:

With 1-methyl-1H-imidazole; zinc; In ethyl acetate; at 80 ℃; for 2h;

Reference yield:

benzoyl chloride (98-88-4) → 1,5-anhydro-2,3,4-tri-O-benzoyl-6-deoxy-D-lyxo-hex-5-enitol (18524-09-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / pyridine / 48 h / 4 - 5 °C

2: 52 percent / NaI / butan-2-one / 5 h / Heating; solvent effect

3: 72 percent / pyridine / DBU / 16 h / 40 °C

With pyridine; sodium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In butanone;

DOI:10.1016/0008-6215(88)84027-8

upstream raw materials:

1,5-anhydro-2,3,4-tri-O-benzoyl-6-deoxy-6-iodo-D-mannitol

1,3,4,5-tetra-O-benzoyl-β-D-fructopyranosyl bromide

1,3,4,5-tetra-O-benzoyl-β-D-fructopyranoside

1,5-anhydro-2,3,4-tri-O-benzoyl-6-O-p-tolylsulfonyl-D-mannitol