(2S,5S)-trans-5-(4-fluorophenoxymethyl)-5-(4-N,O-bis-(phenoxycarbonyl)hydroxylamino-3-butyn-4-yl)tetrahydrofuran

Base Information

Chemical Name:(2S,5S)-trans-5-(4-fluorophenoxymethyl)-5-(4-N,O-bis-(phenoxycarbonyl)hydroxylamino-3-butyn-4-yl)tetrahydrofuran
CAS No.:175212-45-0
Molecular Formula:C₂₉H₂₆FNO₇
Molecular Weight:519.526
Hs Code.:

Synonyms:(2S,5S)-trans-5-(4-fluorophenoxymethyl)-5-(4-N,O-bis-(phenoxycarbonyl)hydroxylamino-3-butyn-4-yl)tetrahydrofuran

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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 (2S,5S)-trans-5-(4-fluorophenoxymethyl)-5-(4-N,O-bis-(phenoxycarbonyl)hydroxylamino-3-butyn-4-yl)tetrahydrofuran

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (2S,5S)-trans-5-(4-fluorophenoxymethyl)-5-(4-N,O-bis-(phenoxycarbonyl)hydroxylamino-3-butyn-4-yl)tetrahydrofuran

There total 23 articles about (2S,5S)-trans-5-(4-fluorophenoxymethyl)-5-(4-N,O-bis-(phenoxycarbonyl)hydroxylamino-3-butyn-4-yl)tetrahydrofuran 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: 92.0%

: 141580-65-6
N,O-Bis(phenoxycarbonyl)hydroxylamine

: 220623-71-2
(2S,5S)-trans-5-((4-fluorophenoxy)methyl)-2-(1-hydroxy-3-butyn-4-yl)tetrahydrofuran

: 175212-45-0
(2S,5S)-trans-5-(4-fluorophenoxymethyl)-5-(4-N,O-bis-(phenoxycarbonyl)hydroxylamino-3-butyn-4-yl)tetrahydrofuran

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1080/00397910008087245

Reference yield:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 175212-45-0
(2S,5S)-trans-5-(4-fluorophenoxymethyl)-5-(4-N,O-bis-(phenoxycarbonyl)hydroxylamino-3-butyn-4-yl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 6 steps

1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 5 h / 20 °C / Reflux; Inert atmosphere; Large scale

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -78 °C / Inert atmosphere; Large scale

3.1: 1H-imidazole; dmap / dichloromethane / 20 °C / Inert atmosphere; Large scale

4.1: trimethylsilyl bromide / dichloromethane / 4 h / -78 °C / Inert atmosphere; Large scale

4.2: 3 h / -78 °C / Inert atmosphere; Large scale

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere; Large scale

6.1: di-isopropyl azodicarboxylate; triphenylphosphine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

With 1H-imidazole; dmap; trimethylsilyl bromide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/op980209l

Reference yield:

: 104605-98-3
(2S)-2-[(4-fluorophenoxy)methyl]oxirane

: 175212-45-0
(2S,5S)-trans-5-(4-fluorophenoxymethyl)-5-(4-N,O-bis-(phenoxycarbonyl)hydroxylamino-3-butyn-4-yl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 7 steps

1.1: Mg / tetrahydrofuran / 0.5 h / 0 °C

1.2: 78 percent / CuCN / tetrahydrofuran / 1 h / 20 °C

2.1: 70 percent / Hg(OCOCF₃)2 / 12 h / 20 °C

3.1: 52 percent / Grubb's catalyst / benzene / 20 h / Heating

4.1: 81 percent / CH₂Cl₂ / 2 h / 20 °C

5.1: i-PrMgBr / tetrahydrofuran / 0.5 h

5.2: ZnBr₂ / tetrahydrofuran / 0.75 h

5.3: tetrahydrofuran / 3 h

6.1: 0.65 g / p-toluenesulfonic acid / methanol / 1 h

7.1: 90 percent / PPh₃; DEAD / tetrahydrofuran / 4 h / 20 °C

With isopropylmagnesium bromide; mercury(II) trifluoroacetate; toluene-4-sulfonic acid; magnesium; triphenylphosphine; diethylazodicarboxylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; dichloromethane; benzene; 1.1: Metallation / 1.2: Addition / 2.1: Etherification / 3.1: Cyclization / 4.1: Addition / 5.1: Metallation / 5.2: Metallation / 5.3: Substitution / 6.1: Methanolysis / 7.1: Condensation;
DOI:10.1055/s-2000-6376