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

Base Information

• Chemical Name: ethyl (2S,3R)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-2-hydroxybutanoate
• CAS No.: 866343-55-7
• Molecular Formula: C₁₇H₂₄O₅
• Molecular Weight: 308.375
• Mol file: 866343-55-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

ethyl (3R)-2-acetoxy-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate (866343-47-7) → ethyl (2S,3R)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-2-hydroxybutanoate (866343-55-7) + ethyl (2R,3R)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-2-hydroxybutanoate (866343-42-2)

Guidance literature:

With sodium ethanolate; In ethanol; at 20 ℃;

DOI:10.1002/chem.200500282

Reference yield: 59.0%

ethyl (3S)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate (326603-47-8) → ethyl (2S,3R)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-2-hydroxybutanoate (866343-55-7) + ethyl (2R,3R)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-2-hydroxybutanoate (866343-42-2)

Guidance literature:

ethyl (3S)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

With MoO₅*pyridine*HMPA; In tetrahydrofuran; at -78 ℃; for 3h;

DOI:10.1002/chem.200500282

Reference yield:

ethyl (2E,4E)-5-phenyl-penta-2,4-dienoate (39806-16-1) → ethyl (2S,3R)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-2-hydroxybutanoate (866343-55-7)

Guidance literature:

Multi-step reaction with 3 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

3.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

3.2: 59 percent / oxodiperoxymolybdenum(pyridine)-hexamethylphosphorictriamide / tetrahydrofuran / 3 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); lithium diisopropyl amide; methanesulfonamide; potassium carbonate; In tetrahydrofuran; diethyl ether; hexane; tert-butyl alcohol;

DOI:10.1002/chem.200500282

upstream raw materials:

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

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

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

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

Downstream raw materials:

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

(2S,3S)-2-(allyoxy)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-butan-1-ol

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

tert-butyl (5R,6S,E)-5-(allyloxy)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-hept-2-enoate