laxogenin-3-yl 2,3-di-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-L-arabinopyranosyl)-D-glucopyranoside

Base Information

• Chemical Name: laxogenin-3-yl 2,3-di-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-L-arabinopyranosyl)-D-glucopyranoside
• CAS No.: 484002-10-0
• Molecular Formula: C₇₃H₈₀O₁₈
• Molecular Weight: 1245.43
• Mol file: 484002-10-0.mol

Synonyms:laxogenin-3-yl 2,3-di-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-L-arabinopyranosyl)-D-glucopyranoside

Chemical Property of laxogenin-3-yl 2,3-di-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-L-arabinopyranosyl)-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of laxogenin-3-yl 2,3-di-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-L-arabinopyranosyl)-D-glucopyranoside

There total 9 articles about laxogenin-3-yl 2,3-di-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-L-arabinopyranosyl)-D-glucopyranoside 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:

3-O-benzyl laxogenin (210687-07-3) → laxogenin-3-yl 2,3-di-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-L-arabinopyranosyl)-D-glucopyranoside (484002-10-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 92 percent / H₂ / Pd/C / CH₂Cl₂; ethanol / 12 h / 20 °C / 760.05 Torr

2: 92 percent / TMSOTf / CH₂Cl₂ / 20 °C

3: 98 percent / NaOMe / methanol; CH₂Cl₂ / 2 h / Heating

4: 90 percent / p-TsOH / dimethylformamide / 3 h / 50 °C / pH 3 - 4

5: 418 mg / pyridine / 1 h / 20 °C

6: 87 percent / p-TsOH / CH₂Cl₂; methanol / 2.5 h / Heating

7: 82 percent / TMSOTf / CH₂Cl₂ / 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium methylate; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo026103c

Reference yield:

3-O-benzyl diosgenin (146333-24-6) → laxogenin-3-yl 2,3-di-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-L-arabinopyranosyl)-D-glucopyranoside (484002-10-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: BH₃*Me₂S / tetrahydrofuran / 12 h / 20 °C

1.2: NaOH; H₂O₂ / tetrahydrofuran; H₂O / 20 °C

1.3: 77 percent / Dess-Martin periodinane / CH₂Cl₂ / 5 h / 20 °C

2.1: 92 percent / H₂ / Pd/C / CH₂Cl₂; ethanol / 12 h / 20 °C / 760.05 Torr

3.1: 92 percent / TMSOTf / CH₂Cl₂ / 20 °C

4.1: 98 percent / NaOMe / methanol; CH₂Cl₂ / 2 h / Heating

5.1: 90 percent / p-TsOH / dimethylformamide / 3 h / 50 °C / pH 3 - 4

6.1: 418 mg / pyridine / 1 h / 20 °C

7.1: 87 percent / p-TsOH / CH₂Cl₂; methanol / 2.5 h / Heating

8.1: 82 percent / TMSOTf / CH₂Cl₂ / 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; hydrogen; sodium methylate; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo026103c

Reference yield:

diosgenin (512-04-9) → laxogenin-3-yl 2,3-di-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-L-arabinopyranosyl)-D-glucopyranoside (484002-10-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaH / tetrahydrofuran; dimethylformamide / 1 h / 20 °C

1.2: 97 percent / tetrahydrofuran; dimethylformamide / Heating

2.1: BH₃*Me₂S / tetrahydrofuran / 12 h / 20 °C

2.2: NaOH; H₂O₂ / tetrahydrofuran; H₂O / 20 °C

2.3: 77 percent / Dess-Martin periodinane / CH₂Cl₂ / 5 h / 20 °C

3.1: 92 percent / H₂ / Pd/C / CH₂Cl₂; ethanol / 12 h / 20 °C / 760.05 Torr

4.1: 92 percent / TMSOTf / CH₂Cl₂ / 20 °C

5.1: 98 percent / NaOMe / methanol; CH₂Cl₂ / 2 h / Heating

6.1: 90 percent / p-TsOH / dimethylformamide / 3 h / 50 °C / pH 3 - 4

7.1: 418 mg / pyridine / 1 h / 20 °C

8.1: 87 percent / p-TsOH / CH₂Cl₂; methanol / 2.5 h / Heating

9.1: 82 percent / TMSOTf / CH₂Cl₂ / 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; hydrogen; sodium methylate; sodium hydride; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo026103c

upstream raw materials:

(25R)-3β-hydroxy-5α-spirostan-6-one

(25R)-3β-(β-D-glucopyranosyloxy)-5α-spirostan-6-one

3-O-benzyl diosgenin

3-O-benzyl laxogenin

Downstream raw materials:

C₉₉H₁₀₀O₂₅

Refernces