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

Base Information

Chemical Name:ethyl (2S,3R,4S)-2,3-isopropylidenedioxy-4-(4-nitrobenzyloxy)-4-phenylbutanoate
CAS No.:252273-55-5
Molecular Formula:C₂₂H₂₃NO₈
Molecular Weight:429.427
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 4 articles about ethyl (2S,3R,4S)-2,3-isopropylidenedioxy-4-(4-nitrobenzyloxy)-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: 97.0%

: 252273-54-4
ethyl (2S,3R,4R)-4-hydroxy-2,3-isopropylidenedioxy-4-phenylbutanoate

: 62-23-7
4-nitro-benzoic acid

: 252273-55-5
ethyl (2S,3R,4S)-2,3-isopropylidenedioxy-4-(4-nitrobenzyloxy)-4-phenylbutanoate

Guidance literature:: With ethyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 1.75h;
DOI:10.1016/S0040-4020(99)00794-2

Reference yield:

: 187931-99-3
ethyl (4S,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate

: 252273-55-5
ethyl (2S,3R,4S)-2,3-isopropylidenedioxy-4-(4-nitrobenzyloxy)-4-phenylbutanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / Et₃N*3HF / acetonitrile / 168 h / 20 °C

2: 97 percent / Ph₃P; ethyl azodicarboxylate / tetrahydrofuran / 1.75 h / 0 - 20 °C

With ethyl azodicarboxylate; triethylamine tris(hydrogen fluoride); triphenylphosphine; In tetrahydrofuran; acetonitrile; 1: desilylation / 2: Mitsunobu reaction;
DOI:10.1016/S0040-4020(99)00794-2

Reference yield:

: 179618-33-8
ethyl (2E,4S)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-4-phenylbut-2-enoate

: 252273-55-5
ethyl (2S,3R,4S)-2,3-isopropylidenedioxy-4-(4-nitrobenzyloxy)-4-phenylbutanoate

Guidance literature:: Multi-step reaction with 4 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

4: 97 percent / Ph₃P; ethyl azodicarboxylate / tetrahydrofuran / 1.75 h / 0 - 20 °C

With ethyl azodicarboxylate; methanesulfonamide; AD-mix-β; camphor-10-sulfonic acid; triethylamine tris(hydrogen fluoride); triphenylphosphine; In tetrahydrofuran; dichloromethane; water; acetonitrile; tert-butyl alcohol; 1: hydroxylation / 2: Cyclization / 3: desilylation / 4: Mitsunobu reaction;
DOI:10.1016/S0040-4020(99)00794-2