4-Nitro-benzoic acid (R)-1-[(2S,4R)-4-((E)-3-ethoxycarbonyl-allyl)-tetrahydro-furan-2-yl]-propyl ester

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Chemical Name:4-Nitro-benzoic acid (R)-1-[(2S,4R)-4-((E)-3-ethoxycarbonyl-allyl)-tetrahydro-furan-2-yl]-propyl ester
CAS No.:871311-00-1
Molecular Formula:C₂₀H₂₅NO₇
Molecular Weight:391.421
Hs Code.:

Synonyms:4-Nitro-benzoic acid (R)-1-[(2S,4R)-4-((E)-3-ethoxycarbonyl-allyl)-tetrahydro-furan-2-yl]-propyl ester

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Chemical Property of 4-Nitro-benzoic acid (R)-1-[(2S,4R)-4-((E)-3-ethoxycarbonyl-allyl)-tetrahydro-furan-2-yl]-propyl ester

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Technology Process of 4-Nitro-benzoic acid (R)-1-[(2S,4R)-4-((E)-3-ethoxycarbonyl-allyl)-tetrahydro-furan-2-yl]-propyl ester

There total 9 articles about 4-Nitro-benzoic acid (R)-1-[(2S,4R)-4-((E)-3-ethoxycarbonyl-allyl)-tetrahydro-furan-2-yl]-propyl ester 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: 78.0%

: 871310-99-5
(E)-4-[(3R,5S)-5-((S)-1-Hydroxy-propyl)-tetrahydro-furan-3-yl]-but-2-enoic acid ethyl ester

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

: 871311-00-1
4-Nitro-benzoic acid (R)-1-[(2S,4R)-4-((E)-3-ethoxycarbonyl-allyl)-tetrahydro-furan-2-yl]-propyl ester

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1016/j.tetlet.2005.09.115

Reference yield:

: 871310-92-8
(S)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-dihydro-furan-2-one

: 871311-00-1
4-Nitro-benzoic acid (R)-1-[(2S,4R)-4-((E)-3-ethoxycarbonyl-allyl)-tetrahydro-furan-2-yl]-propyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: LDA / tetrahydrofuran / 1 h / -78 °C

1.2: tetrahydrofuran / 1 h / -78 °C

2.1: DIBAL / tetrahydrofuran / 0.25 h / -78 °C

3.1: CF₃COOH; Et₃SiH / CH₂Cl₂ / 0.5 h / -40 °C

4.1: OsO₄; NMO / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 1.5 h / 20 °C

4.2: 77 percent / NaIO₄ / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 1 h / 20 °C

5.1: 81 percent / LiCl; DIPEA / acetonitrile / 12 h / 20 °C

6.1: 88 percent / HF / H₂O; acetonitrile / 1 h / 20 °C

7.1: 78 percent / DEAD; Ph₃P / tetrahydrofuran / 2 h / 20 °C

With triethylsilane; osmium(VIII) oxide; N-methyl-2-indolinone; hydrogen fluoride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; lithium chloride; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water; acetonitrile; tert-butyl alcohol; 5.1: Horner-Wadsworth-Emmons olefination / 7.1: Mitsunobu reaction;
DOI:10.1016/j.tetlet.2005.09.115

Reference yield:

: 871310-93-9
{(3S,5S)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-3-yl}-acetaldehyde

: 871311-00-1
4-Nitro-benzoic acid (R)-1-[(2S,4R)-4-((E)-3-ethoxycarbonyl-allyl)-tetrahydro-furan-2-yl]-propyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 81 percent / LiCl; DIPEA / acetonitrile / 12 h / 20 °C

2: 88 percent / HF / H₂O; acetonitrile / 1 h / 20 °C

3: 78 percent / DEAD; Ph₃P / tetrahydrofuran / 2 h / 20 °C

With hydrogen fluoride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; diethylazodicarboxylate; In tetrahydrofuran; water; acetonitrile; 1: Horner-Wadsworth-Emmons olefination / 3: Mitsunobu reaction;
DOI:10.1016/j.tetlet.2005.09.115