(2S,7S)-7-(4-fluorophenoxymethyl)-2-[N,O-bis(phenoxycarbonyl)-3-butyn-4-yl]oxepane

Base Information

• Chemical Name: (2S,7S)-7-(4-fluorophenoxymethyl)-2-[N,O-bis(phenoxycarbonyl)-3-butyn-4-yl]oxepane
• CAS No.: 850453-95-1
• Molecular Formula: C₃₁H₃₀FNO₇
• Molecular Weight: 547.58
• Mol file: 850453-95-1.mol

Synonyms:(2S,7S)-7-(4-fluorophenoxymethyl)-2-[N,O-bis(phenoxycarbonyl)-3-butyn-4-yl]oxepane

Chemical Property of (2S,7S)-7-(4-fluorophenoxymethyl)-2-[N,O-bis(phenoxycarbonyl)-3-butyn-4-yl]oxepane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,7S)-7-(4-fluorophenoxymethyl)-2-[N,O-bis(phenoxycarbonyl)-3-butyn-4-yl]oxepane

There total 7 articles about (2S,7S)-7-(4-fluorophenoxymethyl)-2-[N,O-bis(phenoxycarbonyl)-3-butyn-4-yl]oxepane 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%

N,O-Bis(phenoxycarbonyl)hydroxylamine (141580-65-6) + (2S,7S)-7-(4-fluorophenoxymethyl)-2-(1-hydroxy-3-butyn-4-yl)oxepane (253867-14-0) → (2S,7S)-7-(4-fluorophenoxymethyl)-2-[N,O-bis(phenoxycarbonyl)-3-butyn-4-yl]oxepane (850453-95-1)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1016/j.tetasy.2005.01.024

Reference yield:

(2S)-2-[(4-fluorophenoxy)methyl]oxirane (104605-98-3) → (2S,7S)-7-(4-fluorophenoxymethyl)-2-[N,O-bis(phenoxycarbonyl)-3-butyn-4-yl]oxepane (850453-95-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: magnesium; 1,2-dibromoethane / tetrahydrofuran / 1 h / 20 °C

1.2: 73 percent / cuprous cyanide / tetrahydrofuran / 0.25 h / cooling

2.1: 93 percent / hydrogen / Pd-C / ethanol / 3 h

3.1: 62 percent / 2-iodoxy benzoic acid / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 0 - 20 °C

4.1: 80.8 percent / CaCl₂ / CH₂Cl₂ / 3 h / 0 - 20 °C

5.1: isopropyl magnesium bromide / tetrahydrofuran / 0.5 h

5.2: ZnBr₂ / tetrahydrofuran / 0 °C

5.3: tetrahydrofuran / 12 h

6.1: 1.32 g / p-TSA / methanol / 1 h

7.1: 92 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 4 h / 20 °C

With 2-iodoxybenzoic acid; hydrogen; isopropylmagnesium bromide; toluene-4-sulfonic acid; magnesium; ethylene dibromide; triphenylphosphine; calcium chloride; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; 7.1: Mitsunobu reaction;

DOI:10.1016/j.tetasy.2005.01.024

Reference yield:

(S)-7-benzyloxy-1-(4-fluorophenoxy)heptan-2-ol (253867-10-6) → (2S,7S)-7-(4-fluorophenoxymethyl)-2-[N,O-bis(phenoxycarbonyl)-3-butyn-4-yl]oxepane (850453-95-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 93 percent / hydrogen / Pd-C / ethanol / 3 h

2.1: 62 percent / 2-iodoxy benzoic acid / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 0 - 20 °C

3.1: 80.8 percent / CaCl₂ / CH₂Cl₂ / 3 h / 0 - 20 °C

4.1: isopropyl magnesium bromide / tetrahydrofuran / 0.5 h

4.2: ZnBr₂ / tetrahydrofuran / 0 °C

4.3: tetrahydrofuran / 12 h

5.1: 1.32 g / p-TSA / methanol / 1 h

6.1: 92 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 4 h / 20 °C

With 2-iodoxybenzoic acid; hydrogen; isopropylmagnesium bromide; toluene-4-sulfonic acid; triphenylphosphine; calcium chloride; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; 6.1: Mitsunobu reaction;

DOI:10.1016/j.tetasy.2005.01.024

upstream raw materials:

N,O-Bis(phenoxycarbonyl)hydroxylamine

(2S,7S)-7-(4-fluorophenoxymethyl)-2-(1-hydroxy-3-butyn-4-yl)oxepane

(2S)-2-[(4-fluorophenoxy)methyl]oxirane

(S)-7-(4-fluorophenoxy)-6-hydroxyheptanal