ethyl (3S)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate

Base Information

• Chemical Name: ethyl (3S)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate
• CAS No.: 326603-47-8
• Molecular Formula: C₁₇H₂₄O₄
• Molecular Weight: 292.375
• Mol file: 326603-47-8.mol

Synonyms:ethyl (3S)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate

Chemical Property of ethyl (3S)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (3S)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate

There total 4 articles about ethyl (3S)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate 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: 72.0%

methyllithium (917-54-4) + ethyl (E)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]prop-2-enoate (326603-41-2) → ethyl (3S)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate (326603-47-8)

Guidance literature:

With chloro-trimethyl-silane; In diethyl ether; hexane; at -78 ℃; for 6h;

DOI:10.1002/chem.200500282

Reference yield:

ethyl (2E,4E)-5-phenyl-penta-2,4-dienoate (39806-16-1) → ethyl (3S)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate (326603-47-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1,4-bis-(9-O-dihydroquinidinyl)phthalazine; K₃[Fe(CN)6]; K₂OsO₄*2H₂O / K₂CO₃; CH₃SO₂NH₂ / 2-methyl-propan-2-ol / 0 °C

1.2: 8.732 g / p-TsOH*H₂O / acetone / 20 °C

2.1: 72 percent / Me₃SiCl / diethyl ether; hexane / 6 h / -78 °C

With (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; potassium osmate(VI); chloro-trimethyl-silane; potassium hexacyanoferrate(III); methanesulfonamide; potassium carbonate; In diethyl ether; hexane; tert-butyl alcohol;

DOI:10.1002/chem.200500282

Reference yield:

methyllithium (917-54-4) + ethyl (E)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]prop-2-enoate (326603-41-2) → (R)-ethyl 3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate (326603-45-6) + ethyl (3S)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate (326603-47-8)

Guidance literature:

methyllithium; With copper(l) iodide; In diethyl ether; toluene; at -78 - -40 ℃; for 0.25h;

With boron trifluoride diethyl etherate; In diethyl ether; toluene; at -78 ℃; for 0.25h;

ethyl (E)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]prop-2-enoate; In diethyl ether; toluene; at -78 ℃; for 16h; Further stages. Title compound not separated from byproducts.;

DOI:10.1055/s-2007-1000868

upstream raw materials:

methyllithium

ethyl (E)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]prop-2-enoate

ethyl (2E,4E)-5-phenyl-penta-2,4-dienoate

Downstream raw materials:

ethyl (2S,3R)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-2-hydroxybutanoate

ethyl (2R,3R)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-2-hydroxybutanoate

ethyl (3R)-2-acetoxy-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate

(E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-16-((1R,2R,3R)-2,3-dihydroxy-1-methyl-3-phenyl-propyl)-3-isobutyl-6,6-dimethyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone