7-[(4S,5S)-5-((S)-1-Hydroxy-3-phenyl-prop-2-ynyl)-2-oxo-[1,3]dioxolan-4-yl]-heptanoic acid methyl ester

Base Information

• Chemical Name: 7-[(4S,5S)-5-((S)-1-Hydroxy-3-phenyl-prop-2-ynyl)-2-oxo-[1,3]dioxolan-4-yl]-heptanoic acid methyl ester
• CAS No.: 119324-90-2
• Molecular Formula: C₂₀H₂₄O₆
• Molecular Weight: 360.407
• Mol file: 119324-90-2.mol

Synonyms:

Chemical Property of 7-[(4S,5S)-5-((S)-1-Hydroxy-3-phenyl-prop-2-ynyl)-2-oxo-[1,3]dioxolan-4-yl]-heptanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-[(4S,5S)-5-((S)-1-Hydroxy-3-phenyl-prop-2-ynyl)-2-oxo-[1,3]dioxolan-4-yl]-heptanoic acid methyl ester

There total 10 articles about 7-[(4S,5S)-5-((S)-1-Hydroxy-3-phenyl-prop-2-ynyl)-2-oxo-[1,3]dioxolan-4-yl]-heptanoic acid 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:

copper(I) phenylacetylenide (13146-23-1) → 7-[(4S,5S)-5-((S)-1-Hydroxy-3-phenyl-prop-2-ynyl)-2-oxo-[1,3]dioxolan-4-yl]-heptanoic acid methyl ester (119324-90-2)

Guidance literature:

Multi-step reaction with 2 steps

1: LiI / diethyl ether / Ambient temperature

2: NaBH₄ / methanol / Ambient temperature

With sodium tetrahydroborate; lithium iodide; In methanol; diethyl ether;

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

Reference yield:

cis-Cyclooctene (931-88-4,931-87-3,25267-51-0) → 7-[(4S,5S)-5-((S)-1-Hydroxy-3-phenyl-prop-2-ynyl)-2-oxo-[1,3]dioxolan-4-yl]-heptanoic acid methyl ester (119324-90-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) O₃, 2.) Ac₂O, NEt₃ / 1.) CH₂Cl₂, -78 deg C, 2.) benzene

2: 68 percent / tetrahydrofuran / -78 °C

3: 36 percent / Ti(OiPr)4, L-(+)-DIPT, tBuOOH, 3 Angstroem sieves / CH₂Cl₂ / -20 deg C to room temperature

4: 66 percent / acetonitrile / 168 h / Ambient temperature

5: 69 percent / BF₃*Et₂O / diethyl ether / -20 °C

6: 95 percent / CrO₃, H₂SO₄ / acetone / Ambient temperature

7: oxalyl chloride / CH₂Cl₂ / Ambient temperature

8: LiI / diethyl ether / Ambient temperature

9: NaBH₄ / methanol / Ambient temperature

With chromium(VI) oxide; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; oxalyl dichloride; L-(+)-diisopropyl tartrate; 3 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; acetic anhydride; ozone; triethylamine; lithium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; acetonitrile;

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

Reference yield:

methyl 8-oxooctanoate (3884-92-2) → 7-[(4S,5S)-5-((S)-1-Hydroxy-3-phenyl-prop-2-ynyl)-2-oxo-[1,3]dioxolan-4-yl]-heptanoic acid methyl ester (119324-90-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 68 percent / tetrahydrofuran / -78 °C

2: 36 percent / Ti(OiPr)4, L-(+)-DIPT, tBuOOH, 3 Angstroem sieves / CH₂Cl₂ / -20 deg C to room temperature

3: 66 percent / acetonitrile / 168 h / Ambient temperature

4: 69 percent / BF₃*Et₂O / diethyl ether / -20 °C

5: 95 percent / CrO₃, H₂SO₄ / acetone / Ambient temperature

6: oxalyl chloride / CH₂Cl₂ / Ambient temperature

7: LiI / diethyl ether / Ambient temperature

8: NaBH₄ / methanol / Ambient temperature

With chromium(VI) oxide; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; oxalyl dichloride; L-(+)-diisopropyl tartrate; 3 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; lithium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; acetonitrile;

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

upstream raw materials:

copper(I) phenylacetylenide

cis-Cyclooctene

methyl 8-oxooctanoate

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