(-)-Haplomyrfolin

Base Information

• Chemical Name: (-)-Haplomyrfolin
• CAS No.: 85404-48-4
• Molecular Formula: C₂₀H₂₀O₆
• Molecular Weight: 356.375
• Mol file: 85404-48-4.mol

Synonyms:(3S,4S)-3-Benzo[1,3]dioxol-5-ylmethyl-4-(4-hydroxy-3-methoxy-benzyl)-dihydro-furan-2-one;(-)-Haplomyrfolin;(+/-)-haplomyrfolin;

Chemical Property of (-)-Haplomyrfolin

Chemical Property:

• PSA: 74.22000
• LogP: 2.70390

Purity/Quality:

98% ^*data from raw suppliers

(-)-Haplomyrfolin ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (-)-Haplomyrfolin

There total 18 articles about (-)-Haplomyrfolin 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: 91.0%

(±)-4′-O-benzyl haplomyrfolin → (±)-haplomyrfolin (84755-42-0,85404-48-4)

Guidance literature:

With palladium on activated carbon; hydrogen; In methanol; for 1.5h;

DOI:10.3390/molecules23123057

Reference yield:

(E)-4-(3,4-methylenedioxyphenyl)but-2-en-1-ol (1338823-56-5) → (±)-haplomyrfolin (84755-42-0,85404-48-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: triethylamine / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

1.2: 0.17 h / Inert atmosphere

1.3: 18 h / 20 °C / Inert atmosphere

2.1: titanium(IV) chloride tetrahydrofuran; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / Inert atmosphere

2.2: 18 h / Inert atmosphere

3.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; tert-butyl alcohol; tetrahydrofuran / 120 h / Inert atmosphere

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere

5.1: sodium periodate / water; methanol / 0.33 h / Inert atmosphere

6.1: Fetizon's reagent / toluene / 2 h / Inert atmosphere; Reflux

7.1: palladium on activated carbon; hydrogen / methanol / 1.5 h

With sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; titanium(IV) chloride tetrahydrofuran; palladium on activated carbon; hydrogen; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; toluene; tert-butyl alcohol; 2.1: |Claisen Rearrangement;

DOI:10.3390/molecules23123057

Reference yield:

(E)-4-(4-(3,4-methylenedioxyphenyl)but-2-en-1-yl)morpholine → (±)-haplomyrfolin (84755-42-0,85404-48-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: titanium(IV) chloride tetrahydrofuran; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / Inert atmosphere

1.2: 18 h / Inert atmosphere

2.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; tert-butyl alcohol; tetrahydrofuran / 120 h / Inert atmosphere

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere

4.1: sodium periodate / water; methanol / 0.33 h / Inert atmosphere

5.1: Fetizon's reagent / toluene / 2 h / Inert atmosphere; Reflux

6.1: palladium on activated carbon; hydrogen / methanol / 1.5 h

With sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; titanium(IV) chloride tetrahydrofuran; palladium on activated carbon; hydrogen; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; toluene; tert-butyl alcohol; 1.1: |Claisen Rearrangement;

DOI:10.3390/molecules23123057

upstream raw materials:

3,4-Methylenedioxybenzyl bromide

(hydroxy-4 methoxy-3 benzyl)-4 dihydro-3H-furannone-2

trans-2-(3,4-methylenedioxybenzyl)-3-(4-acetoxy-3-methoxybenzyl)-γ-butyrolactone

(E)-4-(3,4-methylenedioxyphenyl)but-2-en-1-ol

Refernces

• 1、 Ganeshpure,Stevenson. "Synthesis of (±)-pluviatolide and (±)-isopluviatolide". . p. 2175 - 2178. Retrieved 2007/10/02.