4-(5-((benzyloxy)methyl)-4-(benzyloxy)-2,5-dihydro-β-L-furan-2-yl)-3-fluoroaniline

Base Information

Chemical Name:4-(5-((benzyloxy)methyl)-4-(benzyloxy)-2,5-dihydro-β-L-furan-2-yl)-3-fluoroaniline
CAS No.:320592-21-0
Molecular Formula:C₂₅H₂₄FNO₃
Molecular Weight:405.469
Hs Code.:

Synonyms:4-(5-((benzyloxy)methyl)-4-(benzyloxy)-2,5-dihydro-β-L-furan-2-yl)-3-fluoroaniline

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Chemical Property of 4-(5-((benzyloxy)methyl)-4-(benzyloxy)-2,5-dihydro-β-L-furan-2-yl)-3-fluoroaniline

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Technology Process of 4-(5-((benzyloxy)methyl)-4-(benzyloxy)-2,5-dihydro-β-L-furan-2-yl)-3-fluoroaniline

There total 10 articles about 4-(5-((benzyloxy)methyl)-4-(benzyloxy)-2,5-dihydro-β-L-furan-2-yl)-3-fluoroaniline 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: 57.0%

: 656-66-6
3-fluoro-4-iodoaniline

: 320592-15-2
1,4-anhydro-3,5-di-O-benzyl-2-deoxy-L-erythro-pent-1-enitol

: 320592-21-0
4-(5-((benzyloxy)methyl)-4-(benzyloxy)-2,5-dihydro-β-L-furan-2-yl)-3-fluoroaniline

Guidance literature:: With triphenyl-arsane; triethylamine; palladium diacetate; In acetonitrile; at 70 ℃; for 24h;
DOI:10.1021/jo000510b

Reference yield:

: 41546-31-0
L-xylose

: 320592-21-0
4-(5-((benzyloxy)methyl)-4-(benzyloxy)-2,5-dihydro-β-L-furan-2-yl)-3-fluoroaniline

Guidance literature:: Multi-step reaction with 8 steps

1.1: CuSO₄; conc, H₂SO₄ / 4 h / 25 °C

1.2: 98 percent / aq. HCl / 1 h / 25 °C

2.1: 80 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

3.1: 87 percent / PDC; Ac₂O / CH₂Cl₂ / 2 h / Heating

4.1: 28 percent / NaBH₄ / ethanol; ethyl acetate / 1 h / 0 °C

5.1: 92 percent / NaH / tetrahydrofuran / 0 - 25 °C

6.1: aq. AcOH / 5 h / 100 °C

7.1: 1.65 g / Ph₃P; imidazole; I₂ / CH₂Cl₂ / 0.17 h / 25 °C

8.1: 57 percent / Ph₃As; Et₃N / Pd(OAc)2 / acetonitrile / 24 h / 70 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; dipyridinium dichromate; triphenyl-arsane; sulfuric acid; iodine; acetic anhydride; sodium hydride; copper(II) sulfate; acetic acid; triethylamine; triphenylphosphine; palladium diacetate; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1021/jo000510b

Reference yield:

: 114861-22-2
1,2-O-isopropylidene-α-L-xylofuranose

: 320592-21-0
4-(5-((benzyloxy)methyl)-4-(benzyloxy)-2,5-dihydro-β-L-furan-2-yl)-3-fluoroaniline

Guidance literature:: Multi-step reaction with 7 steps

1: 80 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

2: 87 percent / PDC; Ac₂O / CH₂Cl₂ / 2 h / Heating

3: 28 percent / NaBH₄ / ethanol; ethyl acetate / 1 h / 0 °C

4: 92 percent / NaH / tetrahydrofuran / 0 - 25 °C

5: aq. AcOH / 5 h / 100 °C

6: 1.65 g / Ph₃P; imidazole; I₂ / CH₂Cl₂ / 0.17 h / 25 °C

7: 57 percent / Ph₃As; Et₃N / Pd(OAc)2 / acetonitrile / 24 h / 70 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; dipyridinium dichromate; triphenyl-arsane; iodine; acetic anhydride; sodium hydride; acetic acid; triethylamine; triphenylphosphine; palladium diacetate; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1021/jo000510b