Rosellisin

Base Information

• Chemical Name: Rosellisin
• CAS No.: 61486-68-8
• Molecular Formula: C12H14O7
• Molecular Weight: 270.2354
• Hs Code.: 2932209090
• NSC Number: 263672
• Nikkaji Number: J2.867.393K,J20.772A
• ChEMBL ID: CHEMBL4083296
• Mol file: 61486-68-8.mol

Synonyms:ROSELLISIN;NSC263672;Islandic acid II methylester;CHEMBL4083296;BS-1224;NSC-263672

Chemical Property of Rosellisin

Chemical Property:

• Vapor Pressure: 8.7E-14mmHg at 25°C
• Boiling Point: 537.3°Cat760mmHg
• PKA: 13.52±0.10(Predicted)
• Flash Point: 208.6°C
• PSA: 106.20000
• Density: 1.38g/cm³
• LogP: -0.18080
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 270.07395278
• Heavy Atom Count: 19
• Complexity: 471

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=O)OC(=C1CO)C=CC(=O)OC)CO
• Isomeric SMILES: COC1=C(C(=O)OC(=C1CO)/C=C/C(=O)OC)CO

Technology Process of Rosellisin

There total 7 articles about Rosellisin 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: 76.0%

(E)-3-[4-Methoxy-6-oxo-3-(tetrahydro-pyran-2-yloxymethyl)-5-(2-trimethylsilanyl-ethoxymethoxymethyl)-6H-pyran-2-yl]-acrylic acid methyl ester (158205-46-0) → rosellisin (61486-68-8) + (E)-3-[3-Hydroxymethyl-4-methoxy-6-oxo-5-(2-trimethylsilanyl-ethoxymethoxymethyl)-6H-pyran-2-yl]-acrylic acid methyl ester (158205-48-2)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; for 2h; Heating;

DOI:10.3987/COM-93-6568

Reference yield:

5-Chloromethyl-3-hydroxymethyl-4-methoxy-6-methyl-pyran-2-one (158205-39-1) → rosellisin (61486-68-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / i-Pr₂NEt / CH₂Cl₂ / 2 h / 40 °C

2: AgNO₃, 2,6-lutidine / acetone; H₂O / 2 h / 60 °C

3: 99 percent / PPTS / CH₂Cl₂ / 10 h / Ambient temperature

4: 1.) LDA, HPMA / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 90 min

5: 84 percent / p-TsCl, Et₃N, DMAP / CH₂Cl₂ / 2 h / Heating

6: 12 percent / PPTS / methanol / 2 h / Heating

With 2,6-dimethylpyridine; dmap; pyridinium p-toluenesulfonate; silver nitrate; triethylamine; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; lithium diisopropyl amide; In methanol; dichloromethane; water; acetone;

DOI:10.3987/COM-93-6568

Reference yield:

5-Hydroxymethyl-4-methoxy-6-methyl-3-(2-trimethylsilanyl-ethoxymethoxymethyl)-pyran-2-one (158205-42-6) → rosellisin (61486-68-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / PPTS / CH₂Cl₂ / 10 h / Ambient temperature

2: 1.) LDA, HPMA / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 90 min

3: 84 percent / p-TsCl, Et₃N, DMAP / CH₂Cl₂ / 2 h / Heating

4: 12 percent / PPTS / methanol / 2 h / Heating

With dmap; pyridinium p-toluenesulfonate; triethylamine; p-toluenesulfonyl chloride; lithium diisopropyl amide; In methanol; dichloromethane;

DOI:10.3987/COM-93-6568

upstream raw materials:

diazomethane

islandic acid-II

(E)-3-[4-Methoxy-6-oxo-3-(tetrahydro-pyran-2-yloxymethyl)-5-(2-trimethylsilanyl-ethoxymethoxymethyl)-6H-pyran-2-yl]-acrylic acid methyl ester

5-Chloromethyl-3-hydroxymethyl-4-methoxy-6-methyl-pyran-2-one