(S)-4-Benzyl-3-[(1S,2R,3R,4R)-3-(2-benzyloxy-ethyl)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-oxazolidin-2-one

Base Information

• Chemical Name: (S)-4-Benzyl-3-[(1S,2R,3R,4R)-3-(2-benzyloxy-ethyl)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-oxazolidin-2-one
• CAS No.: 128217-42-5
• Molecular Formula: C₂₇H₂₉NO₄
• Molecular Weight: 431.532
• Mol file: 128217-42-5.mol

Synonyms:(S)-4-Benzyl-3-[(1S,2R,3R,4R)-3-(2-benzyloxy-ethyl)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-oxazolidin-2-one

Chemical Property of (S)-4-Benzyl-3-[(1S,2R,3R,4R)-3-(2-benzyloxy-ethyl)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-Benzyl-3-[(1S,2R,3R,4R)-3-(2-benzyloxy-ethyl)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-oxazolidin-2-one

There total 7 articles about (S)-4-Benzyl-3-[(1S,2R,3R,4R)-3-(2-benzyloxy-ethyl)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-oxazolidin-2-one 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%

(4S)-3-((E)-5'-(Benzyloxy)-2'-penetnoyl)-4-(phenylmethyl)-2-oxazolidinone (128217-41-4) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (4S)-3-(((3'R,4'R,5'S,6'S)-5'-(2-(Benzyloxy)ethyl)bicyclo<2.2.1>heptan-4'-yl)carbonyl)-4-(phenylmethyl)-2-oxazolidinone (128217-55-0) + (S)-4-Benzyl-3-[(1S,2R,3R,4R)-3-(2-benzyloxy-ethyl)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-oxazolidin-2-one (128217-42-5) + (S)-4-Benzyl-3-[(1S,2S,3S,4R)-3-(2-benzyloxy-ethyl)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-oxazolidin-2-one (128299-68-3) + (4S)-3-(((3'R,4'R,5'S,6'S)-5'-(2-(Benzyloxy)ethyl)bicyclo<2.2.1>hepten-4'-yl)carbonyl)-4-(phenylmethyl)-2-oxazolidinone (128300-77-6)

Guidance literature:

With diethylaluminium chloride; In dichloromethane; at -78 ℃; for 5h; Yields of byproduct given;

DOI:10.1021/jo00304a019

Reference yield:

2-phenyl-1,3-dioxane (772-01-0) → (S)-4-Benzyl-3-[(1S,2R,3R,4R)-3-(2-benzyloxy-ethyl)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-oxazolidin-2-one (128217-42-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / 1.)diisobutylaluminum hydride, 2.)methanol / toluene / Ambient temperature

2: oxalyl chloride - DMSO, Et₃N / CH₂Cl₂ / 0.75 h / -70 - -65 °C

3: 181.2 g / CH₂Cl₂ / 1.)-70 -> -65 deg C, 15 min., 2.)r.t., 4 h

4: 1N NaOH / tetrahydrofuran / 5 h / Ambient temperature

6: Et₂AlCl / CH₂Cl₂ / 5 h / -78 °C

With methanol; sodium hydroxide; oxalyl dichloride; diethylaluminium chloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/jo00304a019

Reference yield:

3-benzyloxypropan-1-ol (4799-68-2) → (S)-4-Benzyl-3-[(1S,2R,3R,4R)-3-(2-benzyloxy-ethyl)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-oxazolidin-2-one (128217-42-5)

Guidance literature:

Multi-step reaction with 5 steps

1: oxalyl chloride - DMSO, Et₃N / CH₂Cl₂ / 0.75 h / -70 - -65 °C

2: 181.2 g / CH₂Cl₂ / 1.)-70 -> -65 deg C, 15 min., 2.)r.t., 4 h

3: 1N NaOH / tetrahydrofuran / 5 h / Ambient temperature

5: Et₂AlCl / CH₂Cl₂ / 5 h / -78 °C

With sodium hydroxide; oxalyl dichloride; diethylaluminium chloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00304a019

upstream raw materials:

(4S)-3-((E)-5'-(Benzyloxy)-2'-penetnoyl)-4-(phenylmethyl)-2-oxazolidinone

cyclopenta-1,3-diene

2-phenyl-1,3-dioxane

3-benzyloxypropan-1-ol