diethyl 2',3'-di-O-benzoyl-4'-O-methyl-α-L-rhamnopyranosyl-(1->3)-C-(4,6-O-benzylidene-2-acetamido-2-deoxy-α-D-glucopyranosyl)methanephosphonate

Base Information

• Chemical Name: diethyl 2',3'-di-O-benzoyl-4'-O-methyl-α-L-rhamnopyranosyl-(1->3)-C-(4,6-O-benzylidene-2-acetamido-2-deoxy-α-D-glucopyranosyl)methanephosphonate
• CAS No.: 648431-84-9
• Molecular Formula: C₄₁H₅₀NO₁₄P
• Molecular Weight: 811.82
• Mol file: 648431-84-9.mol

Synonyms:

Chemical Property of diethyl 2',3'-di-O-benzoyl-4'-O-methyl-α-L-rhamnopyranosyl-(1->3)-C-(4,6-O-benzylidene-2-acetamido-2-deoxy-α-D-glucopyranosyl)methanephosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diethyl 2',3'-di-O-benzoyl-4'-O-methyl-α-L-rhamnopyranosyl-(1->3)-C-(4,6-O-benzylidene-2-acetamido-2-deoxy-α-D-glucopyranosyl)methanephosphonate

There total 2 articles about diethyl 2',3'-di-O-benzoyl-4'-O-methyl-α-L-rhamnopyranosyl-(1->3)-C-(4,6-O-benzylidene-2-acetamido-2-deoxy-α-D-glucopyranosyl)methanephosphonate 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:

diethyl (((2S,3R,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate (176590-52-6) → diethyl 2',3'-di-O-benzoyl-4'-O-methyl-α-L-rhamnopyranosyl-(1->3)-C-(4,6-O-benzylidene-2-acetamido-2-deoxy-α-D-glucopyranosyl)methanephosphonate (648431-84-9)

Guidance literature:

Multi-step reaction with 3 steps

1: AcOH; H₂ / Pd/C / 3 h / 20 °C

2: 184 mg / p-TsOH*H₂O / dimethylformamide / 1 h / 40 °C

3: 75 percent / molecular sieves 4 Angstroem; N-iodosuccinimide; TMSOTf / CH₂Cl₂ / 20 °C

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen; toluene-4-sulfonic acid; acetic acid; palladium on activated charcoal; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(03)00366-3

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → diethyl 2',3'-di-O-benzoyl-4'-O-methyl-α-L-rhamnopyranosyl-(1->3)-C-(4,6-O-benzylidene-2-acetamido-2-deoxy-α-D-glucopyranosyl)methanephosphonate (648431-84-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 184 mg / p-TsOH*H₂O / dimethylformamide / 1 h / 40 °C

2: 75 percent / molecular sieves 4 Angstroem; N-iodosuccinimide; TMSOTf / CH₂Cl₂ / 20 °C

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(03)00366-3

Reference yield:

diethyl 2',3'-di-O-benzoyl-4'-O-methyl-α-L-rhamnopyranosyl-(1->3)-C-(4,6-O-benzylidene-2-acetamido-2-deoxy-α-D-glucopyranosyl)methanephosphonate (648431-84-9) → C34H46NO14P

Guidance literature:

With acetic acid; In water; at 70 ℃; for 7h;

DOI:10.1016/S0968-0896(03)00366-3

upstream raw materials:

benzaldehyde dimethyl acetal

diethyl (((2S,3R,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate