4-[(2R,3S,5S)-5-(2-Benzyloxy-ethyl)-3-hydroxy-tetrahydro-furan-2-yl]-butyric acid

Base Information

Chemical Name:4-[(2R,3S,5S)-5-(2-Benzyloxy-ethyl)-3-hydroxy-tetrahydro-furan-2-yl]-butyric acid
CAS No.:850656-95-0
Molecular Formula:C₁₇H₂₄O₅
Molecular Weight:308.375
Hs Code.:

Synonyms:4-[(2R,3S,5S)-5-(2-Benzyloxy-ethyl)-3-hydroxy-tetrahydro-furan-2-yl]-butyric acid

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Chemical Property of 4-[(2R,3S,5S)-5-(2-Benzyloxy-ethyl)-3-hydroxy-tetrahydro-furan-2-yl]-butyric acid

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Technology Process of 4-[(2R,3S,5S)-5-(2-Benzyloxy-ethyl)-3-hydroxy-tetrahydro-furan-2-yl]-butyric acid

There total 9 articles about 4-[(2R,3S,5S)-5-(2-Benzyloxy-ethyl)-3-hydroxy-tetrahydro-furan-2-yl]-butyric acid 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:

: 4-[(2R,3S,5S)-5-(2-Benzyloxy-ethyl)-3-hydroxy-tetrahydro-furan-2-yl]-butyraldehyde

: 850656-95-0
4-[(2R,3S,5S)-5-(2-Benzyloxy-ethyl)-3-hydroxy-tetrahydro-furan-2-yl]-butyric acid

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tert-butyl alcohol; at 20 ℃; for 0.75h;
DOI:10.1021/ja042686r

Reference yield:

: 850656-94-9
(2S,3S,5S)-5-(2-Benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carbaldehyde

: 850656-95-0
4-[(2R,3S,5S)-5-(2-Benzyloxy-ethyl)-3-hydroxy-tetrahydro-furan-2-yl]-butyric acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

1.2: 209.1 mg / tetrahydrofuran / 1 h / 0 °C

2.1: 99 percent / H₂ / Pd/C / ethyl acetate; methanol / 5 h / 20 °C

3.1: aq. HCl / tetrahydrofuran / 5 h / 40 - 60 °C

4.1: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.75 h / 20 °C

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; hydrogen; sodium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; tert-butyl alcohol; 1.2: Wittig reaction;
DOI:10.1021/ja042686r

Reference yield:

: 850656-40-5
[(2R,3S,5S)-5-(2-Benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-methanol

: 850656-95-0
4-[(2R,3S,5S)-5-(2-Benzyloxy-ethyl)-3-hydroxy-tetrahydro-furan-2-yl]-butyric acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: SO₃*pyridine; Et₃N; DMSO / CH₂Cl₂ / 1.25 h / 0 °C

2.1: NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

2.2: 209.1 mg / tetrahydrofuran / 1 h / 0 °C

3.1: 99 percent / H₂ / Pd/C / ethyl acetate; methanol / 5 h / 20 °C

4.1: aq. HCl / tetrahydrofuran / 5 h / 40 - 60 °C

5.1: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.75 h / 20 °C

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; pyridine-SO₃ complex; hydrogen; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; tert-butyl alcohol; 1.1: Swern oxidation / 2.2: Wittig reaction;
DOI:10.1021/ja042686r