ethyl (2S,3R,4R)-4-hydroxy-2,3-isopropylidenedioxy-4-phenylbutanoate

Base Information

• Chemical Name: ethyl (2S,3R,4R)-4-hydroxy-2,3-isopropylidenedioxy-4-phenylbutanoate
• CAS No.: 252273-54-4
• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.321
• Mol file: 252273-54-4.mol

Synonyms:ethyl (2S,3R,4R)-4-hydroxy-2,3-isopropylidenedioxy-4-phenylbutanoate

Chemical Property of ethyl (2S,3R,4R)-4-hydroxy-2,3-isopropylidenedioxy-4-phenylbutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2S,3R,4R)-4-hydroxy-2,3-isopropylidenedioxy-4-phenylbutanoate

There total 8 articles about ethyl (2S,3R,4R)-4-hydroxy-2,3-isopropylidenedioxy-4-phenylbutanoate 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: 95.0%

ethyl (4S,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate (187931-99-3) → ethyl (2S,3R,4R)-4-hydroxy-2,3-isopropylidenedioxy-4-phenylbutanoate (252273-54-4)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In acetonitrile; at 20 ℃; for 168h;

DOI:10.1016/S0040-4020(99)00794-2

Reference yield:

C13H16O5 + ethyl iodide (75-03-6) → ethyl (2S,3R,4R)-4-hydroxy-2,3-isopropylidenedioxy-4-phenylbutanoate (252273-54-4)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 25 ℃; for 1h;

DOI:10.1002/asia.202001090

Reference yield:

ethyl (2E,4S)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-4-phenylbut-2-enoate (179618-33-8) → ethyl (2S,3R,4R)-4-hydroxy-2,3-isopropylidenedioxy-4-phenylbutanoate (252273-54-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / AD-mix-β; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 14 h / 20 °C

2: 99 percent / camphorsulfonic acid / CH₂Cl₂ / 0.25 h / 20 °C

3: 95 percent / Et₃N*3HF / acetonitrile / 168 h / 20 °C

With methanesulfonamide; AD-mix-β; camphor-10-sulfonic acid; triethylamine tris(hydrogen fluoride); In dichloromethane; water; acetonitrile; tert-butyl alcohol; 1: hydroxylation / 2: Cyclization / 3: desilylation;

DOI:10.1016/S0040-4020(99)00794-2

upstream raw materials:

ethyl (4S,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate

ethyl (2S,3S,4R)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-2,3-dihydroxy-4-phenylbutanoate

ethyl (2E,4S)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-4-phenylbut-2-enoate

salicylaldehyde

Downstream raw materials:

ethyl (2S,3R,4S)-2,3-isopropylidenedioxy-4-(4-nitrobenzyloxy)-4-phenylbutanoate

ethyl (2S,3R,4S)-4-(t-butyldiphenylsilyloxy)-2,3-isopropylidenedioxy-4-phenylbutanoate

trimethyl [5S,6S,7S]-7-(t-butyldiphenylsilyloxy)-5,6-isopropylidenedioxy-4-oxo-7-phenyl-3-phenylsulfonylorthoheptanoate

ethyl (2S,3R,4S)-4-hydroxy-2,3-isopropylidenedioxy-4-phenylbutanoate