Pregomisin

Base Information

• Chemical Name: Pregomisin
• CAS No.: 66280-26-0
• Molecular Formula: C22H30O6
• Molecular Weight: 390.477
• UNII: 5AYW92EXLG
• DSSTox Substance ID: DTXSID601045554
• Nikkaji Number: J239.389A
• Wikipedia: Pregomisin
• Wikidata: Q15424795
• Metabolomics Workbench ID: 121753
• ChEMBL ID: CHEMBL1081697
• Mol file: 66280-26-0.mol

Synonyms:Pregomisin;66280-26-0;UNII-5AYW92EXLG;5AYW92EXLG;5-[(2S,3R)-4-(3-hydroxy-4,5-dimethoxyphenyl)-2,3-dimethylbutyl]-2,3-dimethoxyphenol;3,3'-DIHYDROXY-4,4',5,5'-TETRAMETHOXYLIGNAN;Pre-Gomisin;PHENOL, 3,3'-((2R,3S)-2,3-DIMETHYL-1,4-BUTANEDIYL)BIS(5,6-DIMETHOXY-, REL-;PHENOL, 3,3'-(2,3-DIMETHYL-1,4-BUTANEDIYL)BIS(5,6-DIMETHOXY-, (R*,S*)-;CHEMBL1081697;DTXSID601045554;AKOS040762218;Q15424795;3,3'-[(2R,3S)-2,3-Dimethyl-1,4-butanediyl]bis(5,6-dimethoxyphenol);5-[(2R,3S)-4-(3-hydroxy-4,5-dimethoxyphenyl)-2,3-dimethylbutyl]-2,3-dimethoxyphenol;5-[(2S,3R)-4-(3-hydroxy-4,5-dimethoxy-phenyl)-2,3-dimethyl-butyl]-2,3-dimethoxy-phenol

Chemical Property of Pregomisin

Chemical Property:

• Vapor Pressure: 1.69E-12mmHg at 25°C
• Boiling Point: 545.2°C at 760 mmHg
• PKA: 9.35±0.15(Predicted)
• Flash Point: 283.6°C
• PSA: 77.38000
• Density: 1.139g/cm³
• LogP: 4.18960
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 390.20423867
• Heavy Atom Count: 28
• Complexity: 407

Purity/Quality:

98.5% ^*data from raw suppliers

Pregomisin 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC1=CC(=C(C(=C1)OC)OC)O)C(C)CC2=CC(=C(C(=C2)OC)OC)O
• Isomeric SMILES: C[C@H](CC1=CC(=C(C(=C1)OC)OC)O)[C@@H](C)CC2=CC(=C(C(=C2)OC)OC)O

Technology Process of Pregomisin

There total 10 articles about Pregomisin 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: 65.0%

C36H42O6 → 5-[(2S,3R)-4-(3-hydroxy-4,5-dimethoxyphenyl)-2,3-dimethylbutyl]-2,3-dimethoxyphenol (66280-26-0)

Guidance literature:

With palladium on activated charcoal; hydrogen; In tetrahydrofuran; at 20 ℃; for 15h;

DOI:10.1002/chem.202100804

Reference yield:

(8R,8'S)-dihydroguaiaretic acid (36469-60-0,121209-88-9,124649-78-1,66322-34-7) → 5-[(2S,3R)-4-(3-hydroxy-4,5-dimethoxyphenyl)-2,3-dimethylbutyl]-2,3-dimethoxyphenol (66280-26-0)

Guidance literature:

Multi-step reaction with 3 steps

1: HNO₃, AcOH / ethyl acetate

2: K₂CO₃ / acetone

3: (i) Sn, HCl, (ii) HNO₂, (iii) aq. H₂SO₄

With nitric acid; potassium carbonate; acetic acid; In ethyl acetate; acetone;

DOI:10.1248/cpb.26.682

Reference yield:

Guaiaretsaeure → 5-[(2S,3R)-4-(3-hydroxy-4,5-dimethoxyphenyl)-2,3-dimethylbutyl]-2,3-dimethoxyphenol (66280-26-0)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / Pd-C / methanol

2: HNO₃, AcOH / ethyl acetate

3: K₂CO₃ / acetone

4: Sn, aq. HCl / ethanol; CHCl₃

5: (i) aq. NaNO₂, H₂SO₄, DMSO, (ii) aq. H₂SO₄

With hydrogenchloride; tin; hydrogen; nitric acid; potassium carbonate; acetic acid; palladium on activated charcoal; In methanol; ethanol; chloroform; ethyl acetate; acetone;

DOI:10.1248/cpb.27.1583

upstream raw materials:

2,3-dimethyl-1,4-di(3,4-dimethoxy-5-nitro-phenyl)butane

2,3-dimethyl-1,4-di(3-methoxy-4-hydroxy-5-nitro-phenyl)butane

(8R,8'S)-dihydroguaiaretic acid

Downstream raw materials:

5,5'-(2,3-dimethylbutane-1,4-diyl)bis(1,2,3-trimethoxybenzene)