(19E)-19,20-Didehydrocuran-17,18-diol

Base Information

• Chemical Name: (19E)-19,20-Didehydrocuran-17,18-diol
• CAS No.: 900-98-1
• Molecular Formula: C19H24N2O2
• Molecular Weight: 312.41
• Mol file: 900-98-1.mol

Synonyms:(19E)-19,20-Didehydrocuran-17,18-diol

Chemical Property of (19E)-19,20-Didehydrocuran-17,18-diol

Chemical Property:

• Melting Point: 251 - 253 °C (aq. ethanol)
• PSA: 55.73000
• LogP: 1.42940

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (19E)-19,20-Didehydrocuran-17,18-diol

There total 15 articles about (19E)-19,20-Didehydrocuran-17,18-diol 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:

methyl 18-hydroxy-2β,16β-cur-19-en-17-oate (55968-99-5) → (-)-Wieland-Gumlich aldehyde (724794-46-1) + N(1)-desacetyl 18-hydroxyisoretuline (900-98-1)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -90 ℃; Title compound not separated from byproducts;

DOI:10.1021/ja00126a017

Reference yield:

(-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-(E)-<(hydroxymethyl)methylene>-1H-pyrrolo<2,3-d>carbazole-6-carboxylates (152425-19-9) → N(1)-desacetyl 18-hydroxyisoretuline (900-98-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) 10percent H₂SO₄, Zn, 2.) NaOMe / 1.) MeOH, reflux, 45 min, 2.) MeOH, RT, 9 h

2: DIBALH / CH₂Cl₂ / -90 °C

With sulfuric acid; sodium methylate; diisobutylaluminium hydride; zinc; In dichloromethane;

DOI:10.1021/ja00126a017

Reference yield:

(1S,3R,5R)-3-<1(E)-(1-(hydroxymethyl)-3-tert-butoxypropenyl)>-1-<1-<2-<5-(1,3-dimethylhexahydro-2-oxo-1,3,5-triazinyl)>phenyl>ethenyl>-6-oxabicyclo<3.1.0>hexane (152425-15-5) → N(1)-desacetyl 18-hydroxyisoretuline (900-98-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) diisopropylethylamine, MsCl, 2.) LiCl / 1.) CH₂Cl₂, -23 deg C, 1 h, 2.) CH₂Cl₂, DMF, -23 deg C to RT

2: 1.) NaH / 1.) DMF, RT, 30 min, 2.) DMF, RT, 12 h

3: NaH / benzene / 48 h / 100 °C

4: KOH / ethanol; H₂O / 3 h / 70 °C

5: 98 percent / Na₂SO₄ / acetonitrile / 0.17 h / Heating

6: 1.) LDA / 1.) THF, hexane, 0 deg C, 0.5 h, 2.) THF, hexane, -78 deg C, 2 h

7: 10percent HCl (gas) / methanol / 12 h / Heating

8: 1.) 10percent H₂SO₄, Zn, 2.) NaOMe / 1.) MeOH, reflux, 45 min, 2.) MeOH, RT, 9 h

9: DIBALH / CH₂Cl₂ / -90 °C

With hydrogenchloride; potassium hydroxide; sulfuric acid; sodium methylate; sodium hydride; diisobutylaluminium hydride; methanesulfonyl chloride; sodium sulfate; N-ethyl-N,N-diisopropylamine; lithium chloride; zinc; lithium diisopropyl amide; In methanol; ethanol; dichloromethane; water; acetonitrile; benzene;

DOI:10.1021/ja00126a017

upstream raw materials:

N⁽¹⁾-desacetyl 18-acetoxyisoretuline

methyl 18-hydroxy-2β,16β-cur-19-en-17-oate

(-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-(E)-<(hydroxymethyl)methylene>-1H-pyrrolo<2,3-d>carbazole-6-carboxylates

(1S,3R,5R)-3-<1(E)-(1-(hydroxymethyl)-3-tert-butoxypropenyl)>-1-<1-<2-<5-(1,3-dimethylhexahydro-2-oxo-1,3,5-triazinyl)>phenyl>ethenyl>-6-oxabicyclo<3.1.0>hexane

Downstream raw materials:

N-desacetylisoretuline

Refernces