(2R,5R)-trans-5-((4-fluorophenoxy)methyl)-2-(1-[N,O-bis(phenoxycarbonyl)hydroxylamino]-3-butyn-4-yl)tetrahydrofuran

Base Information

• Chemical Name: (2R,5R)-trans-5-((4-fluorophenoxy)methyl)-2-(1-[N,O-bis(phenoxycarbonyl)hydroxylamino]-3-butyn-4-yl)tetrahydrofuran
• CAS No.: 851532-62-2
• Molecular Formula: C₂₉H₂₆FNO₇
• Molecular Weight: 519.526

Synonyms:(2R,5R)-trans-5-((4-fluorophenoxy)methyl)-2-(1-[N,O-bis(phenoxycarbonyl)hydroxylamino]-3-butyn-4-yl)tetrahydrofuran

Chemical Property of (2R,5R)-trans-5-((4-fluorophenoxy)methyl)-2-(1-[N,O-bis(phenoxycarbonyl)hydroxylamino]-3-butyn-4-yl)tetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5R)-trans-5-((4-fluorophenoxy)methyl)-2-(1-[N,O-bis(phenoxycarbonyl)hydroxylamino]-3-butyn-4-yl)tetrahydrofuran

There total 12 articles about (2R,5R)-trans-5-((4-fluorophenoxy)methyl)-2-(1-[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: 76.0%

N,O-Bis(phenoxycarbonyl)hydroxylamine (141580-65-6) + (2R,5R)-trans-5-((4-fluorophenoxy)methyl)-2-(1-hydroxy-3-butyn-4-yl)tetrahydrofuran (851532-61-1) → (2R,5R)-trans-5-((4-fluorophenoxy)methyl)-2-(1-[N,O-bis(phenoxycarbonyl)hydroxylamino]-3-butyn-4-yl)tetrahydrofuran (851532-62-2)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; at 0 - 20 ℃; for 1h;

DOI:10.1016/j.tetasy.2005.01.045

Reference yield:

ethyl (R,Z)-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)acrylate (36326-38-2,64520-58-7,91057-97-5,91926-90-8,104321-62-2,124818-64-0,128525-67-7,128525-69-9,104321-63-3,917877-01-1) → (2R,5R)-trans-5-((4-fluorophenoxy)methyl)-2-(1-[N,O-bis(phenoxycarbonyl)hydroxylamino]-3-butyn-4-yl)tetrahydrofuran (851532-62-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 99 percent / H₂ / PtO₂ / ethyl acetate / 4 h / 20 °C

2.1: 97 percent / LiAlH₄ / tetrahydrofuran / 3 h / 0 - 20 °C

3.1: IBX / dimethylsulfoxide / 4 h / 0 - 20 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.2: 55 percent / tetrahydrofuran; hexane / -78 - 20 °C

5.1: 77 percent / Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

6.1: 89 percent / acetic acid / H₂O / 12 h / 20 °C

7.1: 81 percent / Et₃N / CH₂Cl₂ / 10 h / 20 °C

8.1: 98 percent / K₂CO₃ / methanol / 3 h / 20 °C

9.1: 65 percent / Et₃N / CH₂Cl₂ / 8 h / 20 °C

10.1: 94 percent / NaH / dimethylformamide / 5 h / 80 °C

11.1: DDQ / CH₂Cl₂; H₂O / 5 h / 20 °C

12.1: 76 percent / PPh₃; DIAD / CH₂Cl₂ / 1 h / 0 - 20 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; di-isopropyl azodicarboxylate; hydrogen; sodium hydride; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; platinum(IV) oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; 12.1: Mitsunobu reaction;

DOI:10.1016/j.tetasy.2005.01.045

Reference yield:

(R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propanal (133008-09-0) → (2R,5R)-trans-5-((4-fluorophenoxy)methyl)-2-(1-[N,O-bis(phenoxycarbonyl)hydroxylamino]-3-butyn-4-yl)tetrahydrofuran (851532-62-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 55 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 77 percent / Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

3.1: 89 percent / acetic acid / H₂O / 12 h / 20 °C

4.1: 81 percent / Et₃N / CH₂Cl₂ / 10 h / 20 °C

5.1: 98 percent / K₂CO₃ / methanol / 3 h / 20 °C

6.1: 65 percent / Et₃N / CH₂Cl₂ / 8 h / 20 °C

7.1: 94 percent / NaH / dimethylformamide / 5 h / 80 °C

8.1: DDQ / CH₂Cl₂; H₂O / 5 h / 20 °C

9.1: 76 percent / PPh₃; DIAD / CH₂Cl₂ / 1 h / 0 - 20 °C

With dmap; n-butyllithium; di-isopropyl azodicarboxylate; sodium hydride; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; 9.1: Mitsunobu reaction;

DOI:10.1016/j.tetasy.2005.01.045

upstream raw materials:

N,O-Bis(phenoxycarbonyl)hydroxylamine

(2R,5R)-trans-5-((4-fluorophenoxy)methyl)-2-(1-hydroxy-3-butyn-4-yl)tetrahydrofuran

(R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propanal

ethyl (R,Z)-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)acrylate

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