Isoolivil

Base Information

• Chemical Name: Isoolivil
• CAS No.: 3064-05-9
• Molecular Formula: C₂₀H₂₄O₇
• Molecular Weight: 376.406
• DSSTox Substance ID: DTXSID101347745
• Nikkaji Number: J22.576B
• Wikidata: Q104396243
• Metabolomics Workbench ID: 141409
• ChEMBL ID: CHEMBL516536
• Mol file: 3064-05-9.mol

Synonyms:cycloolivil

Chemical Property of Isoolivil

Chemical Property:

• Melting Point: 175-176℃ (methanol )
• PSA: 119.61000
• LogP: 1.13490
• Storage Temp.: ?20°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 376.15220310
• Heavy Atom Count: 27
• Complexity: 489

Purity/Quality:

99% ^*data from raw suppliers

Cycloolivil 95+% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: N
• Statements: 50
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(C(C(CC2=C1)(CO)O)CO)C3=CC(=C(C=C3)O)OC)O
• Isomeric SMILES: COC1=C(C=C2[C@@H]([C@H]([C@@](CC2=C1)(CO)O)CO)C3=CC(=C(C=C3)O)OC)O

Technology Process of Isoolivil

There total 16 articles about Isoolivil 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: 98.0%

(2S,3S,4S)-6-(benzyloxy)-4-(4-(benzyloxy)-3-methoxyphenyl)-2-(hydroxymethyl)-7-methoxy-3-((naphthalen-2-ylmethoxy)methyl)-1,2,3,4-tetrahydronaphthalen-2-ol → cycloolivil (3064-05-9,110150-30-6)

Guidance literature:

With hydrogen; palladium(II) hydroxide; In methanol; ethyl acetate; for 4h;

DOI:10.1021/acs.orglett.0c00773

Reference yield:

1-(4-(benzyloxy)-3-methoxyphenyl)prop-2-en-1-ol → cycloolivil (3064-05-9,110150-30-6)

Guidance literature:

Multi-step reaction with 14 steps

1.1: lipase acrylic resin / toluene / 40 °C / Molecular sieve; Enzymatic reaction

2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

3.1: Grubbs catalyst first generation / dichloromethane / 2 h / 40 °C / Inert atmosphere

4.1: copper(l) iodide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

4.2: 1 h / -78 °C / Inert atmosphere

4.3: 0.17 h / 0 °C

5.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

5.2: 1 h / -78 °C / Inert atmosphere

6.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 °C / Inert atmosphere

7.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone; water / 8 h / 20 °C

8.1: periodic acid / tetrahydrofuran / 1 h / 0 °C

9.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 °C

10.1: sodium hydride / N,N-dimethyl-formamide / 1.5 h / 20 °C / Inert atmosphere

11.1: potassium hexamethylsilazane / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere

11.2: 1 h / -78 °C / Inert atmosphere

11.3: 20 °C / Inert atmosphere

12.1: diisobutylaluminium hydride / 0 °C

13.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

14.1: palladium(II) hydroxide; hydrogen / methanol; ethyl acetate / 4 h

With Grubbs catalyst first generation; triethylsilane; sodium tetrahydroborate; copper(l) iodide; osmium(VIII) oxide; lipase acrylic resin; boron trifluoride diethyl etherate; hydrogen; palladium(II) hydroxide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; periodic acid; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/acs.orglett.0c00773

Reference yield:

(S)-5-(4-(benzyloxy)-3-methoxyphenyl)furan-2(5H)-one → cycloolivil (3064-05-9,110150-30-6)

Guidance literature:

Multi-step reaction with 11 steps

1.1: copper(l) iodide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 °C / Inert atmosphere

1.3: 0.17 h / 0 °C

2.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 °C / Inert atmosphere

3.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 °C / Inert atmosphere

4.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone; water / 8 h / 20 °C

5.1: periodic acid / tetrahydrofuran / 1 h / 0 °C

6.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 °C

7.1: sodium hydride / N,N-dimethyl-formamide / 1.5 h / 20 °C / Inert atmosphere

8.1: potassium hexamethylsilazane / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere

8.2: 1 h / -78 °C / Inert atmosphere

8.3: 20 °C / Inert atmosphere

9.1: diisobutylaluminium hydride / 0 °C

10.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

11.1: palladium(II) hydroxide; hydrogen / methanol; ethyl acetate / 4 h

With triethylsilane; sodium tetrahydroborate; copper(l) iodide; osmium(VIII) oxide; boron trifluoride diethyl etherate; hydrogen; palladium(II) hydroxide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; periodic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone;

DOI:10.1021/acs.orglett.0c00773

upstream raw materials:

3-methoxy-4-(phenylmethoxy)benzaldehyde

Downstream raw materials:

iso-olivil dimethyl ether

benzene-1,2-diol

Refernces