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

Base Information

• Chemical Name: 3-O-allyl-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl chloride
• CAS No.: 101528-48-7
• Molecular Formula: C₂₃H₂₅ClO₅
• Molecular Weight: 416.901
• Mol file: 101528-48-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 3-O-allyl-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl chloride 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:

1-O-acetyl-3-O-allyl-2-O-benzoyl-4-O-benzyl-α/β-L-rhamnopyranose (101528-46-5,101528-47-6) → 3-O-allyl-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl chloride (101528-48-7)

Guidance literature:

With Dichloromethyl methyl ether; zinc dibromide; In dichloromethane; for 0.25h;

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:

3-O-allyl-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl chloride (101528-48-7) → methyl 2-O-(2-O-benzoyl-4-benzyl-α-L-rhamnopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside (101528-58-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / tetramethylurea, Ag trifluoromethanesulphonate / CH₂Cl₂ / 3 h / -70 °C / slow warming to r.t.

2: 64 percent / tris(triphenylphosphine)Rh(I)chloride / ethanol; H₂O / 4.5 h / 80 °C

With Wilkinson's catalyst; silver trifluoromethanesulfonate; tetramethylurea; In ethanol; dichloromethane; water;

upstream raw materials:

1-O-acetyl-3-O-allyl-2-O-benzoyl-4-O-benzyl-α/β-L-rhamnopyranose

Downstream raw materials:

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

methyl 2-O-(3-O-allyl-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-3-O-allyl-4-O-benzyl-α-L-rhamnopyranoside

methyl 2-O-(2-O-benzoyl-4-benzyl-α-L-rhamnopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside