(3S,5R)-3-((E)-But-2-enyl)-3-(3,4-dimethoxy-phenyl)-5-hydroxymethyl-dihydro-furan-2-one

Base Information

• Chemical Name: (3S,5R)-3-((E)-But-2-enyl)-3-(3,4-dimethoxy-phenyl)-5-hydroxymethyl-dihydro-furan-2-one
• CAS No.: 81309-83-3
• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.359
• Mol file: 81309-83-3.mol

Synonyms:(3S,5R)-3-((E)-But-2-enyl)-3-(3,4-dimethoxy-phenyl)-5-hydroxymethyl-dihydro-furan-2-one

Chemical Property of (3S,5R)-3-((E)-But-2-enyl)-3-(3,4-dimethoxy-phenyl)-5-hydroxymethyl-dihydro-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5R)-3-((E)-But-2-enyl)-3-(3,4-dimethoxy-phenyl)-5-hydroxymethyl-dihydro-furan-2-one

There total 4 articles about (3S,5R)-3-((E)-But-2-enyl)-3-(3,4-dimethoxy-phenyl)-5-hydroxymethyl-dihydro-furan-2-one 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:

(3R,5R)-5-Benzyloxymethyl-3-((E)-but-2-enyl)-3-(3,4-dimethoxy-phenyl)-dihydro-furan-2-one (81309-82-2) → (3S,5R)-3-((E)-But-2-enyl)-3-(3,4-dimethoxy-phenyl)-5-hydroxymethyl-dihydro-furan-2-one (81309-83-3)

Guidance literature:

With hydrogenchloride; In ethanol; for 3h; Yield given; Heating;

DOI:10.1016/S0040-4039(01)93019-9

Reference yield:

3,4-dimethoxyphenylacetonitrile (93-17-4) → (3S,5R)-3-((E)-But-2-enyl)-3-(3,4-dimethoxy-phenyl)-5-hydroxymethyl-dihydro-furan-2-one (81309-83-3)

Guidance literature:

Multi-step reaction with 4 steps

1: LDA / tetrahydrofuran / -78 - 20 °C

2: 1.) 10percent KOH-EtOH, 2.) 10percent HCl-EtOH / 1.) reflux over night, 2.) room temperature

3: 1.) lithium diisopropylamide / tetrahydrofuran / from -78 degC up to room temperature

4: c.HCl / ethanol / 3 h / Heating

With hydrogenchloride; potassium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; ethanol;

DOI:10.1016/S0040-4039(01)93019-9

Reference yield:

(R)-5-Benzyloxymethyl-3-(3,4-dimethoxy-phenyl)-dihydro-furan-2-one (81309-80-0,81309-81-1) → (3S,5R)-3-((E)-But-2-enyl)-3-(3,4-dimethoxy-phenyl)-5-hydroxymethyl-dihydro-furan-2-one (81309-83-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) lithium diisopropylamide / tetrahydrofuran / from -78 degC up to room temperature

2: c.HCl / ethanol / 3 h / Heating

With hydrogenchloride; lithium diisopropyl amide; In tetrahydrofuran; ethanol;

DOI:10.1016/S0040-4039(01)93019-9

upstream raw materials:

(3R,5R)-5-Benzyloxymethyl-3-((E)-but-2-enyl)-3-(3,4-dimethoxy-phenyl)-dihydro-furan-2-one

3,4-dimethoxyphenylacetonitrile

(R)-5-Benzyloxymethyl-3-(3,4-dimethoxy-phenyl)-dihydro-furan-2-one

(R)-5-Benzyloxy-2-(3,4-dimethoxy-phenyl)-4-hydroxy-pentanenitrile

Downstream raw materials:

(3S,5S)-3-((E)-But-2-enyl)-3-(3,4-dimethoxy-phenyl)-5-hydroxy-dihydro-furan-2-one

(-)-mesembrine

(S)-3-((E)-But-2-enyl)-3-(3,4-dimethoxy-phenyl)-dihydro-furan-2-one

(S)-4-(3,4-Dimethoxy-phenyl)-4-(2-hydroxy-ethyl)-3-methylamino-cyclohex-2-enone