EV-22 methyl ester

Base Information

• Chemical Name: EV-22 methyl ester
• CAS No.: 115216-95-0
• Molecular Formula: C₁₈H₂₀O₆
• Molecular Weight: 332.353
• DSSTox Substance ID: DTXSID70921652

Synonyms:EV-22 methyl ester;Sch 31828 methyl ester;BRN 4271675;L 663992;1,3-Dioxolane-4-heptanoic acid, 5-(1-hydroxy-2,4,6-heptatriynyl)-2-oxo-, methyl ester, (4S-(4-alpha,5-beta(S*)))-;115216-95-0;DTXSID70921652;LS-62566;METHYL 7-[5-(1-HYDROXYHEPTA-2,4,6-TRIYN-1-YL)-2-OXO-1,3-DIOXOLAN-4-YL]HEPTANOATE

Chemical Property of EV-22 methyl ester

Chemical Property:

• Vapor Pressure: 1.18E-12mmHg at 25°C
• Boiling Point: 512.6°C at 760 mmHg
• Flash Point: 182.2°C
• PSA: 82.06000
• Density: 1.215g/cm³
• LogP: 1.40490
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 332.12598835
• Heavy Atom Count: 24
• Complexity: 629

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCCCCCC1C(OC(=O)O1)C(C#CC#CC#C)O

Technology Process of EV-22 methyl ester

There total 24 articles about EV-22 methyl ester 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: 80.0%

5-(1(R)-hydroxy-7-(trimethylsilyl)-2,4,6-heptatriynyl)-2-oxo-4(S),5(S)-1,3-dioxolane-4-heptanoic acid, methyl ester (119259-01-7) → triyne carbonate L-660,661 methylester (115216-95-0)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)86037-2

Reference yield:

(hex-5-enyl)magnesium bromide (30043-41-5) → triyne carbonate L-660,661 methylester (115216-95-0)

Guidance literature:

Multi-step reaction with 17 steps

1: diethyl ether; tetrahydrofuran / Ambient temperature

2: OsO₄/NaIO₄ / tetrahydrofuran; H₂O / Ambient temperature

3: benzene / Ambient temperature

4: H₂ / Pd-C / ethanol / 1551.4 Torr / Ambient temperature

5: conc. HCl / 0 °C

6: H₂SO₄, CuSO / Ambient temperature

7: 1.) BF₃*Et₂O, HgO (red) 2.) NaBH₄ / 1.) THF, r.t. 2.) EtOH, r.t.

8: Ph₃P, CCl₄ / Heating

9: LiOH / H₂O; 1,2-dimethoxy-ethane / Ambient temperature

10: LDA / tetrahydrofuran / -25 °C

11: NaH / tetrahydrofuran / Ambient temperature

12: 1.5 N HCl / H₂O; tetrahydrofuran / Ambient temperature

13: diethyl ether

14: benzene / Ambient temperature

15: CuCl, TMEDA, O₂ / acetone / 0.02 h / Ambient temperature

16: DDQ / H₂O; CH₂Cl₂ / Ambient temperature

17: n-Bu₄NF / tetrahydrofuran; acetic acid

With hydrogenchloride; tetrachloromethane; lithium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; oxygen; sodium hydride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(l) chloride; mercury(II) oxide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; water; acetic acid; acetone; benzene;

DOI:10.1016/S0040-4039(00)97810-9

Reference yield:

(S)-6-((3aR,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-6-hydroxy-hexanal (131425-24-6) → triyne carbonate L-660,661 methylester (115216-95-0)

Guidance literature:

Multi-step reaction with 15 steps

1: benzene / Ambient temperature

2: H₂ / Pd-C / ethanol / 1551.4 Torr / Ambient temperature

3: conc. HCl / 0 °C

4: H₂SO₄, CuSO / Ambient temperature

5: 1.) BF₃*Et₂O, HgO (red) 2.) NaBH₄ / 1.) THF, r.t. 2.) EtOH, r.t.

6: Ph₃P, CCl₄ / Heating

7: LiOH / H₂O; 1,2-dimethoxy-ethane / Ambient temperature

8: LDA / tetrahydrofuran / -25 °C

9: NaH / tetrahydrofuran / Ambient temperature

10: 1.5 N HCl / H₂O; tetrahydrofuran / Ambient temperature

11: diethyl ether

12: benzene / Ambient temperature

13: CuCl, TMEDA, O₂ / acetone / 0.02 h / Ambient temperature

14: DDQ / H₂O; CH₂Cl₂ / Ambient temperature

15: n-Bu₄NF / tetrahydrofuran; acetic acid

With hydrogenchloride; tetrachloromethane; lithium hydroxide; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; oxygen; sodium hydride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(l) chloride; mercury(II) oxide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; water; acetic acid; acetone; benzene;

DOI:10.1016/S0040-4039(00)97810-9

upstream raw materials:

5-(1(R)-hydroxy-7-(trimethylsilyl)-2,4,6-heptatriynyl)-2-oxo-4(S),5(S)-1,3-dioxolane-4-heptanoic acid, methyl ester

cis-Cyclooctene

methyl 8-oxooctanoate

7-((4S,5R)-5-Formyl-2-oxo-[1,3]dioxolan-4-yl)-heptanoic acid methyl ester

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