benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3-O-benzoyl-α-L-arabinopyranoside

Base Information

• Chemical Name: benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3-O-benzoyl-α-L-arabinopyranoside
• CAS No.: 875878-30-1
• Molecular Formula: C₇₆H₈₈O₁₅
• Molecular Weight: 1241.53
• Mol file: 875878-30-1.mol

Synonyms:benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3-O-benzoyl-α-L-arabinopyranoside

Chemical Property of benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3-O-benzoyl-α-L-arabinopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3-O-benzoyl-α-L-arabinopyranoside

There total 12 articles about benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3-O-benzoyl-α-L-arabinopyranoside 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:

benzyl 3-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranosyl)-oleanolate (875878-36-7) + benzoyl chloride (98-88-4) → benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3-O-benzoyl-α-L-arabinopyranoside (875878-30-1) + benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→2)-4-O-benzoyl-α-L-arabinopyranoside (1637228-47-7)

Guidance literature:

benzyl 3-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranosyl)-oleanolate; With di(n-butyl)tin oxide; In toluene; for 1h; Reflux;

benzoyl chloride; In toluene; for 4h; Overall yield = 94 %; Overall yield = 309 mg;

DOI:10.3390/molecules181215193

Reference yield:

10-[5-acetoxy-4-benzoyloxy-3-(3,4,5-tris-benzoyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid benzyl ester → benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3-O-benzoyl-α-L-arabinopyranoside (875878-30-1)

Guidance literature:

With acetyl chloride; In methanol; dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.carres.2005.10.015

Reference yield:

benzyl oleanolate 3-O-3′,4′-O-isopropylidene-α-L-arabinopyranoside (875878-34-5) → benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3-O-benzoyl-α-L-arabinopyranoside (875878-30-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 79 percent / 4 Angstroem molecular sieves; BF₃*Et₂O / CH₂Cl₂ / 2 h / -78 °C

2: 98 percent / TsOH / CH₂Cl₂; methanol / 20 °C

3: TsOH / toluene / 1 h / 20 °C

4: 262 mg / acetic acid; H₂O / 1 h / 20 °C

5: pyridine / 20 °C

6: 187 mg / AcCl / CH₂Cl₂; methanol / 0 - 20 °C

With 4 A molecular sieve; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; acetyl chloride; In pyridine; methanol; dichloromethane; water; acetic acid; toluene;

DOI:10.1016/j.carres.2005.10.015

upstream raw materials:

benzyl oleanolate 3-O-3′,4′-O-isopropylidene-α-L-arabinopyranoside

3-O-β-D-arabinopyranose oleanolic acid benzyl ester

benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-arabinopyranoside

benzyl 3-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranosyl)-oleanolate

Downstream raw materials:

benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→2)-4-O-benzoyl-α-L-arabinopyranoside