Benzoic acid (2R,3R,4R,5S,6S)-4-allyloxy-2-((2R,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-5-benzyloxy-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,4R,5S,6S)-4-allyloxy-2-((2R,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-5-benzyloxy-6-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 101528-57-8
• Molecular Formula: C₄₀H₄₈O₁₀
• Molecular Weight: 688.815
• Mol file: 101528-57-8.mol

Synonyms:Benzoic acid (2R,3R,4R,5S,6S)-4-allyloxy-2-((2R,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-5-benzyloxy-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2R,3R,4R,5S,6S)-4-allyloxy-2-((2R,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-5-benzyloxy-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3R,4R,5S,6S)-4-allyloxy-2-((2R,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-5-benzyloxy-6-methyl-tetrahydro-pyran-3-yl ester

There total 8 articles about Benzoic acid (2R,3R,4R,5S,6S)-4-allyloxy-2-((2R,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-5-benzyloxy-6-methyl-tetrahydro-pyran-3-yl ester 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: 78.0%

methyl 3-O-allyl-4-O-benzyl-α-L-rhamnopyranoside (69558-09-4) + 3-O-allyl-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl chloride (101528-48-7) → Benzoic acid (2R,3R,4R,5S,6S)-4-allyloxy-2-((2R,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-5-benzyloxy-6-methyl-tetrahydro-pyran-3-yl ester (101528-57-8) + methyl 2-O-(3-O-allyl-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-3-O-allyl-4-O-benzyl-α-L-rhamnopyranoside (101528-56-7)

Guidance literature:

With silver trifluoromethanesulfonate; tetramethylurea; In dichloromethane; at -70 ℃; for 3h; slow warming to r.t.;

Reference yield:

methyl 4-O-benzyl-α-L-rhamnopyranoside (25019-69-6) → Benzoic acid (2R,3R,4R,5S,6S)-4-allyloxy-2-((2R,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-5-benzyloxy-6-methyl-tetrahydro-pyran-3-yl ester (101528-57-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / toluene-p-sulphonic acid, triethylamine / dimethylformamide / 0.67 h / 50 °C

2: 81.6 percent / trifluoromethansulphonic acid / CCl₄; cyclohexane / 18 h / Ambient temperature

3: 80 percent / Na-methoxide / methanol

4: 4.5 percent / tetramethylurea, Ag trifluoromethanesulphonate / CH₂Cl₂ / 3 h / -70 °C / slow warming to r.t.

With trifluorormethanesulfonic acid; sodium methylate; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; triethylamine; tetramethylurea; In methanol; tetrachloromethane; dichloromethane; cyclohexane; N,N-dimethyl-formamide;

Reference yield:

methyl 2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside (90164-70-8) → Benzoic acid (2R,3R,4R,5S,6S)-4-allyloxy-2-((2R,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-5-benzyloxy-6-methyl-tetrahydro-pyran-3-yl ester (101528-57-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 81.6 percent / trifluoromethansulphonic acid / CCl₄; cyclohexane / 18 h / Ambient temperature

2: 80 percent / Na-methoxide / methanol

3: 4.5 percent / tetramethylurea, Ag trifluoromethanesulphonate / CH₂Cl₂ / 3 h / -70 °C / slow warming to r.t.

With trifluorormethanesulfonic acid; sodium methylate; silver trifluoromethanesulfonate; tetramethylurea; In methanol; tetrachloromethane; dichloromethane; cyclohexane;

upstream raw materials:

methyl 3-O-allyl-4-O-benzyl-α-L-rhamnopyranoside

3-O-allyl-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl chloride

methyl 4-O-benzyl-α-L-rhamnopyranoside

methyl 2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside