(S)-1-[(2R,4R)-4-(2-oxoethyl)tetrahydrofuran-2-yl]propyl p-nitrobenzoate

Base Information

Chemical Name:(S)-1-[(2R,4R)-4-(2-oxoethyl)tetrahydrofuran-2-yl]propyl p-nitrobenzoate
CAS No.:865487-09-8
Molecular Formula:C₁₆H₁₉NO₆
Molecular Weight:321.33
Hs Code.:

Synonyms:(S)-1-[(2R,4R)-4-(2-oxoethyl)tetrahydrofuran-2-yl]propyl p-nitrobenzoate

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Chemical Property of (S)-1-[(2R,4R)-4-(2-oxoethyl)tetrahydrofuran-2-yl]propyl p-nitrobenzoate

Chemical Property:

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Technology Process of (S)-1-[(2R,4R)-4-(2-oxoethyl)tetrahydrofuran-2-yl]propyl p-nitrobenzoate

There total 8 articles about (S)-1-[(2R,4R)-4-(2-oxoethyl)tetrahydrofuran-2-yl]propyl p-nitrobenzoate 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: 85.0%

: 865487-11-2
(S)-1-[(2R,4S)-4-allyltetrahydrofuran-2-yl]propyl p-nitrobenzoate

: 865487-09-8
(S)-1-[(2R,4R)-4-(2-oxoethyl)tetrahydrofuran-2-yl]propyl p-nitrobenzoate

Guidance literature:: (S)-1-[(2R,4S)-4-allyltetrahydrofuran-2-yl]propyl p-nitrobenzoate; With ozone; In methanol; at -78 ℃; for 0.0833333h;

With dimethylsulfide; In methanol; at -78 - 20 ℃; for 2h;
DOI:10.1016/j.tetlet.2005.07.041

Reference yield:

: 54340-70-4
ethyl (E)-4-heptenoic acid ester

: 865487-09-8
(S)-1-[(2R,4R)-4-(2-oxoethyl)tetrahydrofuran-2-yl]propyl p-nitrobenzoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: CH3CO2NH2 / AD-mix-β / 2-methyl-propan-2-ol; H2O / 12 h / 0 °C

1.2: 89 percent / TsOH*H₂O / CH₂Cl₂ / 1 h / 20 °C

2.1: 75 percent / imidazole / dimethylformamide / 19 h / 20 °C

3.1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -78 °C

4.1: DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

5.1: Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 8 h / -78 - -5 °C

6.1: TBAF / tetrahydrofuran / 48 h / 20 °C

7.1: PPh₃; DEAD / toluene / 48 h / 20 °C

8.1: O₃ / methanol / 0.08 h / -78 °C

8.2: 85 percent / Me₂S / methanol / 2 h / -78 - 20 °C

With 1H-imidazole; triethylsilane; (O-carboxymethyl)hydroxylamine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; ozone; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; AD-mix-β; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.1: Sharpless asymmetric dihydroxylation / 7.1: Mitsunobu inversion;
DOI:10.1016/j.tetlet.2005.07.041

Reference yield:

: (1R)-1-[(2R,4S)-4-allyltetrahydrofuran-2-yl]-1-propanol

: 865487-09-8
(S)-1-[(2R,4R)-4-(2-oxoethyl)tetrahydrofuran-2-yl]propyl p-nitrobenzoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: PPh₃; DEAD / toluene / 48 h / 20 °C

2.1: O₃ / methanol / 0.08 h / -78 °C

2.2: 85 percent / Me₂S / methanol / 2 h / -78 - 20 °C

With ozone; triphenylphosphine; diethylazodicarboxylate; In methanol; toluene; 1.1: Mitsunobu inversion;
DOI:10.1016/j.tetlet.2005.07.041