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

Base Information

• Chemical Name: benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→2)-3,4-O-isopropylidene-α-L-arabinopyranoside
• CAS No.: 1355346-19-8
• Molecular Formula: C₅₇H₈₂O₁₄
• Molecular Weight: 991.27
• Mol file: 1355346-19-8.mol

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

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

There total 4 articles about benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→2)-3,4-O-isopropylidene-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 oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-arabinopyranoside (875878-32-3) → benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→2)-3,4-O-isopropylidene-α-L-arabinopyranoside (1355346-19-8)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium methylate / methanol; dichloromethane / 2 h / 20 °C

2: toluene-4-sulfonic acid / acetone / 4 h

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 20 °C / Molecular sieve

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; toluene-4-sulfonic acid; In methanol; dichloromethane; acetone;

DOI:10.3390/molecules181215193

Reference yield:

oleanolic acid benzyl ester (303114-51-4) → benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→2)-3,4-O-isopropylidene-α-L-arabinopyranoside (1355346-19-8)

Guidance literature:

Multi-step reaction with 4 steps

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 20 °C / Molecular sieve

2: sodium methylate / methanol; dichloromethane / 2 h / 20 °C

3: toluene-4-sulfonic acid / acetone / 4 h

4: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 20 °C / Molecular sieve

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; toluene-4-sulfonic acid; In methanol; dichloromethane; acetone;

DOI:10.3390/molecules181215193

Reference yield:

2,3,4-tri-O-benzoyl-β-L-arabinopyranosyl trichloroacetimidate-4C1 (247017-34-1) → benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→2)-3,4-O-isopropylidene-α-L-arabinopyranoside (1355346-19-8)

Guidance literature:

Multi-step reaction with 4 steps

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 20 °C / Molecular sieve

2: sodium methylate / methanol; dichloromethane / 2 h / 20 °C

3: toluene-4-sulfonic acid / acetone / 4 h

4: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 20 °C / Molecular sieve

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; toluene-4-sulfonic acid; In methanol; dichloromethane; acetone;

DOI:10.3390/molecules181215193

upstream raw materials:

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

oleanolic acid benzyl ester

2,3,4-tri-O-benzoyl-β-L-arabinopyranosyl trichloroacetimidate-⁴C₁

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

Downstream raw materials:

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

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

Refernces

• 1、 Ren, Li,Liu, Yong-Xiang,Lv, Dan,Yan, Mao-Cai,Nie, Han,Liu, Yang,Cheng, Mao-Sheng. "Facile synthesis of the naturally cytotoxic triterpenoid saponin patrinia-glycoside B-II and its conformer". . p. 15193 - 15206. Retrieved 2014/01/17.