3-O-Benzoyl-1,2-O-[1-(exo-methoxycarbonyl)ethylidene]-β-L-rhamnopyranose

Base Information

• Chemical Name: 3-O-Benzoyl-1,2-O-[1-(exo-methoxycarbonyl)ethylidene]-β-L-rhamnopyranose
• CAS No.: 197246-63-2
• Molecular Formula: C₁₇H₂₀O₈
• Molecular Weight: 352.341
• Mol file: 197246-63-2.mol

Synonyms:3-O-Benzoyl-1,2-O-[1-(exo-methoxycarbonyl)ethylidene]-β-L-rhamnopyranose

Chemical Property of 3-O-Benzoyl-1,2-O-[1-(exo-methoxycarbonyl)ethylidene]-β-L-rhamnopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-Benzoyl-1,2-O-[1-(exo-methoxycarbonyl)ethylidene]-β-L-rhamnopyranose

There total 1 articles about 3-O-Benzoyl-1,2-O-[1-(exo-methoxycarbonyl)ethylidene]-β-L-rhamnopyranose 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: 58.0%

benzoyl cyanide (613-90-1) + 1,2-O-<1-(exo-methoxycarbonyl)ethylidene>-β-L-rhamnopyranose (113829-53-1) → 4-O-benzoyl-1,2-O-<1-(exo-methoxycarbonyl)ethylidene>-β-L-rhamnopyranose (113757-33-8) + 3-O-Benzoyl-1,2-O-[1-(exo-methoxycarbonyl)ethylidene]-β-L-rhamnopyranose (197246-63-2) + (2S,3aR,5S,6S,7R,7aR)-6,7-Bis-benzoyloxy-2,5-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-2-carboxylic acid methyl ester

Guidance literature:

With pyridine; at 20 ℃; for 18h; Title compound not separated from byproducts;

DOI:10.1002/chem.19970030818

Reference yield: 65.0%

3-O-Benzoyl-1,2-O-[1-(exo-methoxycarbonyl)ethylidene]-β-L-rhamnopyranose (197246-63-2) + 2,3-Di-O-benzoyl-4-O-chloroacetyl-α-D-rhamnopyranosyl bromide (185992-26-1) → 4-O-(4-O-Chloroacetyl-2,3-di-O-benzoyl-α-D-rhamnopyranosyl)-3-O-benzoyl-1,2-O-[1-(exo-methoxycarbonyl)ethylidene]-β-L-rhamnopyranose (197246-72-3)

Guidance literature:

With 2,3,5-trimethyl-pyridine; silver trifluoromethanesulfonate; In dichloromethane; at -30 - 20 ℃; for 1h;

DOI:10.1002/chem.19970030818

Reference yield:

3-O-Benzoyl-1,2-O-[1-(exo-methoxycarbonyl)ethylidene]-β-L-rhamnopyranose (197246-63-2) → 3-O-Benzoyl-4-O-(2,3-di-O-benzoyl-4-O-trityl-α-D-rhamnopyranosyl)-1,2-O-[1-(exo-methoxycarbonyl)ethylidene]-β-L-rhamnopyranose (197246-76-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / AgOTf, collidine / CH₂Cl₂ / 1 h / -30 - 20 °C

2: 91 percent / aq. (NH₂)2CS / acetonitrile / 40 h / 20 °C

3: 84 percent / collidine / CH₂Cl₂ / 2 h / 20 °C

With 2,3,5-trimethyl-pyridine; silver trifluoromethanesulfonate; thiourea; In dichloromethane; acetonitrile;

DOI:10.1002/chem.19970030818

upstream raw materials:

benzoyl cyanide

1,2-O-<1-(exo-methoxycarbonyl)ethylidene>-β-L-rhamnopyranose

Downstream raw materials:

4-O-(4-O-Chloroacetyl-2,3-di-O-benzoyl-α-D-rhamnopyranosyl)-3-O-benzoyl-1,2-O-[1-(exo-methoxycarbonyl)ethylidene]-β-L-rhamnopyranose

3-O-Benzoyl-4-O-(2,3-di-O-benzoyl-α-D-rhamnopyranosyl)-1,2-O-[1-(exo-methoxycarbonyl)ethylidene]-β-L-rhamnopyranose

3-O-Benzoyl-4-O-(2,3-di-O-benzoyl-4-O-trityl-α-D-rhamnopyranosyl)-1,2-O-[1-(exo-cyano)ethylidene]-β-L-rhamnopyranose

3-O-Benzoyl-4-O-(2,3-di-O-benzoyl-4-O-trityl-α-D-rhamnopyranosyl)-1,2-O-[1-(exo-methoxycarbonyl)ethylidene]-β-L-rhamnopyranose