2-O-acetyl-1,5-anhydro-4-O-benzoyl-3-O-benzyl-6-deoxy-L-arabino-hex-1-enitol

Base Information

• Chemical Name: 2-O-acetyl-1,5-anhydro-4-O-benzoyl-3-O-benzyl-6-deoxy-L-arabino-hex-1-enitol
• CAS No.: 194347-79-0
• Molecular Formula: C₂₂H₂₂O₆
• Molecular Weight: 382.413
• Mol file: 194347-79-0.mol

Synonyms:2-O-acetyl-1,5-anhydro-4-O-benzoyl-3-O-benzyl-6-deoxy-L-arabino-hex-1-enitol

Chemical Property of 2-O-acetyl-1,5-anhydro-4-O-benzoyl-3-O-benzyl-6-deoxy-L-arabino-hex-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-acetyl-1,5-anhydro-4-O-benzoyl-3-O-benzyl-6-deoxy-L-arabino-hex-1-enitol

There total 10 articles about 2-O-acetyl-1,5-anhydro-4-O-benzoyl-3-O-benzyl-6-deoxy-L-arabino-hex-1-enitol 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: 85.0%

4-O-benzoyl-3-O-benzyl-1,2-O-[1-(exo-methoxy)ethylidene]-L-rhamnopyranose → 2-O-acetyl-1,5-anhydro-4-O-benzoyl-3-O-benzyl-6-deoxy-L-arabino-hex-1-enitol (194347-79-0)

Guidance literature:

With pyridine; In various solvent(s); for 3h; Heating;

DOI:10.1002/ejoc.200300149

Reference yield: 82.0%

Benzoic acid (2S,3aR,5S,6S,7R,7aR)-7-benzyloxy-2-methoxy-2,5-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester (615541-10-1) → 2-O-acetyl-1,5-anhydro-4-O-benzoyl-3-O-benzyl-6-deoxy-L-arabino-hex-1-enitol (194347-79-0)

Guidance literature:

With pyridine; In various solvent(s); for 5h; Heating;

DOI:10.1016/S0040-4039(97)01225-2

Reference yield:

methyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (115678-10-9) → 2-O-acetyl-1,5-anhydro-4-O-benzoyl-3-O-benzyl-6-deoxy-L-arabino-hex-1-enitol (194347-79-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 98 percent / pyridine / 17 h / 20 °C

2.1: 85 percent / trifluoroacetic acid / methanol / 4.5 °C / Heating

3.1: n-dibuthyltin oxide / benzene / 5 h / Heating

3.2: n-tetrabutylammonium iodide / benzene / 6 h / 50 °C

3.3: 70 percent / pyridine / 0.33 h / 0 - 20 °C

4.1: bromine / CH₂Cl₂ / 0 °C

4.2: 68 percent / 2,6-lutidine / CH₂Cl₂ / 19 h / 50 °C

5.1: 85 percent / pyridine / various solvent(s) / 3 h / Heating

With pyridine; bromine; di(n-butyl)tin oxide; trifluoroacetic acid; In pyridine; methanol; dichloromethane; benzene;

DOI:10.1002/ejoc.200300149

upstream raw materials:

Benzoic acid (2S,3aR,5S,6S,7R,7aR)-7-benzyloxy-2-methoxy-2,5-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester

benzyl bromide

benzoyl chloride

methyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

Downstream raw materials:

isopropyl 4-O-benzoyl-3-O-benzyl-6-deoxy-β-L-arabino-hexopyranosid-2-ulose

methyl 2,3-O-isopropylidene-4-O-(2-O-acetyl-4-O-benzoyl-β-L-rhamnopyranosyl)-α-L-rhamnopyranoside

methyl 2,3-O-isopropylidene-4-O-(4-O-benzoyl-3-O-benzyl-β-L-rhamnopyranosyl)-α-L-rhamnopyranoside

methyl 2,3-O-isopropylidene-4-O-(2-O-acetyl-4-O-benzoyl-3-O-benzyl-β-L-rhamnopyranosyl)-α-L-rhamnopyranoside