(-)-O-benzylepitrachelogenine

Base Information

• Chemical Name: (-)-O-benzylepitrachelogenine
• CAS No.: 124988-55-2
• Molecular Formula: C₂₈H₃₀O₇
• Molecular Weight: 478.542
• Mol file: 124988-55-2.mol

Synonyms:(-)-O-benzylepitrachelogenine

Chemical Property of (-)-O-benzylepitrachelogenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-O-benzylepitrachelogenine

There total 3 articles about (-)-O-benzylepitrachelogenine 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: 24.0%

(3R,4R)-3-[(3-methoxy-4-benzyloxyphenyl)methyl]-4-[(3,4-dimethoxyphenyl)methyl] dihydro-2-(3H)-furanone (123251-05-8) → (-)-O-benzylepitrachelogenine (124988-55-2) + (-)-O-benzyltrachelogenine (124887-01-0)

Guidance literature:

With oxygen; lithium hexamethyldisilazane; (1,4,7,10-tetraoxacyclododecane); In benzene; for 3h; Ambient temperature;

DOI:10.1016/S0040-4039(00)99653-9

Reference yield:

(R)-4-(3,4-dimethoxybenzyl)dihydrofuran-2(3H)-one (108102-77-8) → (-)-O-benzylepitrachelogenine (124988-55-2)

Guidance literature:

Multi-step reaction with 2 steps

2: 21 percent / lithium hexamethyldisilazide, dry oxygen / 12-crown-4 / benzene / 3 h / Ambient temperature

With oxygen; lithium hexamethyldisilazane; (1,4,7,10-tetraoxacyclododecane); In benzene;

DOI:10.1016/S0040-4039(00)99653-9

Reference yield:

1-(benzyloxy)-4-(bromomethyl)-2-methoxybenzene (72724-00-6) → (3R,4R)-3-(4-Benzyloxy-3-methoxy-benzyl)-4-(3,4-dimethoxy-benzyl)-3-hydroxy-dihydro-furan-2-one (124887-01-0,124988-55-2,131351-74-1,131351-75-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) lithium diisopropylamide / 1.) THF, 2.) THF

2: 1.) potassium bis(trimethylsilyl)amide, 18-crown-6, 2.) oxodiperoxymolybdenum(pyridine)(hexamethylphosphorictriamide) / 1.) THF, -100 deg C, 30 min, 2.) THF, 1-2 h

With MoO₅*pyridine*HMPA; 18-crown-6 ether; potassium hexamethylsilazane; lithium diisopropyl amide;

DOI:10.1021/jo9601932

upstream raw materials:

1-(benzyloxy)-4-(bromomethyl)-2-methoxybenzene

(3R,4R)-3-[(3-methoxy-4-benzyloxyphenyl)methyl]-4-[(3,4-dimethoxyphenyl)methyl] dihydro-2-(3H)-furanone

(R)-4-(3,4-dimethoxybenzyl)dihydrofuran-2(3H)-one

Downstream raw materials:

(-)-epitrachelogenine