rac-di-O-benzyl-latifine

Base Information

• Chemical Name: rac-di-O-benzyl-latifine
• CAS No.: 97455-98-6
• Molecular Formula: C₃₁H₃₁NO₃
• Molecular Weight: 465.592
• Mol file: 97455-98-6.mol

Synonyms:rac-di-O-benzyl-latifine

Chemical Property of rac-di-O-benzyl-latifine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of rac-di-O-benzyl-latifine

There total 16 articles about rac-di-O-benzyl-latifine 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:

5-Benzyloxy-4-(4-benzyloxy-phenyl)-6-methoxy-2-methyl-3,4-dihydro-isoquinolinium; chloride (97455-99-7) → rac-di-O-benzyl-latifine (97455-98-6)

Guidance literature:

With sodium tetrahydroborate; In methanol; water; at 0 ℃; for 1h; Yield given;

Reference yield:

p-benzyloxybenzaldehyde (4397-53-9) → rac-di-O-benzyl-latifine (97455-98-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) NaH; 2.) DIBAL / 1.) THF, 0 deg C; 2.) toluene, 0 deg C

2: 34 percent / diethyl azodicarboxylate, triphenylphosphine

3: 75 percent / N,N-dimethylaniline / 0.83 h / Heating

4: 83 percent / K₂CO₃ / dimethylformamide / 9 h / 80 °C

5: 1.) O₃; 2.) sodium borohydride / 1.) MeOH, CH₂Cl₂, -78 deg C, 12 min; 2.) -78 deg C to r.t.

6: 86 percent / diethyl azodicarboxylate, triphenylphosphine

7: 96 percent / hydrazine hydrate / ethanol / 2.5 h / Heating

8: 90 percent / 0.75 h / 0 deg C to r.t.

9: 89 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / Heating

10: 85 percent / 1 h / 0 deg C to r.t.

11: phosphorus oxychloride / benzene / 0.75 h / Heating

12: sodium borohydride / methanol / 1 h / 0 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ozone; hydrazine hydrate; N,N-dimethyl-aniline; triphenylphosphine; diethylazodicarboxylate; trichlorophosphate; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; benzene;

DOI:10.1246/cl.1985.505

Reference yield:

rac-6-(4-benzyloxy-α-vinylbenzyl)guiacol (97456-01-4) → rac-di-O-benzyl-latifine (97455-98-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 83 percent / K₂CO₃ / dimethylformamide / 9 h / 80 °C

2: 1.) O₃; 2.) sodium borohydride / 1.) MeOH, CH₂Cl₂, -78 deg C, 12 min; 2.) -78 deg C to r.t.

3: 86 percent / diethyl azodicarboxylate, triphenylphosphine

4: 96 percent / hydrazine hydrate / ethanol / 2.5 h / Heating

5: 90 percent / 0.75 h / 0 deg C to r.t.

6: 89 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / Heating

7: 85 percent / 1 h / 0 deg C to r.t.

8: phosphorus oxychloride / benzene / 0.75 h / Heating

9: sodium borohydride / methanol / 1 h / 0 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; potassium carbonate; ozone; hydrazine hydrate; triphenylphosphine; diethylazodicarboxylate; trichlorophosphate; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; benzene;

DOI:10.1246/cl.1985.505

upstream raw materials:

5-Benzyloxy-4-(4-benzyloxy-phenyl)-6-methoxy-2-methyl-3,4-dihydro-isoquinolinium; chloride

p-benzyloxybenzaldehyde

rac-6-(4-benzyloxy-α-vinylbenzyl)guiacol

rac-3-(4-benzyloxyphenyl)-3-(2-benzyloxy-3-methoxyphenyl)prop-1-ene

Downstream raw materials:

(+/-)-latifine