p-nitrophenyl 4-O-benzyl-2-O-<4-O-(2,4-di-O-benzyl-3,6-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranosyl>-3-O-methyl-α-L-rhamnopryranoside

Base Information

• Chemical Name: p-nitrophenyl 4-O-benzyl-2-O-<4-O-(2,4-di-O-benzyl-3,6-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranosyl>-3-O-methyl-α-L-rhamnopryranoside
• CAS No.: 150424-95-6
• Molecular Formula: C₅₀H₆₃NO₁₆
• Molecular Weight: 934.047
• Mol file: 150424-95-6.mol

Synonyms:

Chemical Property of p-nitrophenyl 4-O-benzyl-2-O-<4-O-(2,4-di-O-benzyl-3,6-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranosyl>-3-O-methyl-α-L-rhamnopryranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrophenyl 4-O-benzyl-2-O-<4-O-(2,4-di-O-benzyl-3,6-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranosyl>-3-O-methyl-α-L-rhamnopryranoside

There total 7 articles about p-nitrophenyl 4-O-benzyl-2-O-<4-O-(2,4-di-O-benzyl-3,6-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranosyl>-3-O-methyl-α-L-rhamnopryranoside 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: 56.7%

p-nitrophenyl 4-O-benzyl-3-O-methyl-α-L-rhamnopyranoside (150412-47-8) + methyl 4-O-(2,4-di-O-benzyl-3,6-di-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-1-thio-α-L-rhamnopyranoside → p-nitrophenyl 4-O-benzyl-2-O-<4-O-(2,4-di-O-benzyl-3,6-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranosyl>-3-O-methyl-α-L-rhamnopryranoside (150424-95-6)

Guidance literature:

With 4 A molecular sieve; methyl trifluoromethanesulfonate; In dichloromethane; for 20h;

DOI:10.1016/0008-6215(93)80099-Z

Reference yield: 56.7%

p-nitrophenyl 4-O-benzyl-3-O-methyl-α-L-rhamnopyranoside (150412-47-8) + ethyl 4-O-(2,4-di-O-benzyl-3,6-di-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-1-thio-α-L-rhamnopyranoside (150412-61-6) → p-nitrophenyl 4-O-benzyl-2-O-<4-O-(2,4-di-O-benzyl-3,6-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranosyl>-3-O-methyl-α-L-rhamnopryranoside (150424-95-6)

Guidance literature:

With 4 A molecular sieve; methyl trifluoromethanesulfonate; In dichloromethane;

DOI:10.1016/0008-6215(93)80099-Z

Reference yield:

benzyl bromide (100-39-0) → p-nitrophenyl 4-O-benzyl-2-O-<4-O-(2,4-di-O-benzyl-3,6-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranosyl>-3-O-methyl-α-L-rhamnopryranoside (150424-95-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 72.2 percent / KOH / dimethylformamide / 4 h / 0 °C

2: 96.8 percent / trifluoroacetic acid, water / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 1.) dibutyltin oxide / 1.) benzene, reflux, 3 h, 2.) DMF, 50 deg C, overnight

4: 56.7 percent / methyl triflate, molecular sieves 4 Angstroem / CH₂Cl₂ / 20 h

With potassium hydroxide; 4 A molecular sieve; water; di(n-butyl)tin oxide; trifluoroacetic acid; methyl trifluoromethanesulfonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(93)80099-Z

upstream raw materials:

p-nitrophenyl 4-O-benzyl-3-O-methyl-α-L-rhamnopyranoside

ethyl 4-O-(2,4-di-O-benzyl-3,6-di-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-1-thio-α-L-rhamnopyranoside

benzyl bromide

p-nitrophenyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

Downstream raw materials:

4-{(2S,3R,4R,5S,6S)-5-Benzyloxy-3-[(2S,3R,4R,5S,6S)-5-((2S,3R,4S,5R,6R)-3,5-bis-benzyloxy-4-methoxy-6-methoxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy]-4-methoxy-6-methyl-tetrahydro-pyran-2-yloxy}-phenylamine

p-trifluoroacetamidophenyl 4-O-benzyl-2-O-<4-O-(2,4-di-O-benzyl-3,6-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranosyl>-3-O-methyl-α-L-rhamnopryranoside