(Z)-7-((1R,2S,3S,4R,6S)-3-Benzenesulfonylamino-6-hydroxy-bicyclo[2.2.1]hept-2-yl)-hept-5-enoic acid methyl ester

Base Information

• Chemical Name: (Z)-7-((1R,2S,3S,4R,6S)-3-Benzenesulfonylamino-6-hydroxy-bicyclo[2.2.1]hept-2-yl)-hept-5-enoic acid methyl ester
• CAS No.: 146324-53-0
• Molecular Formula: C₂₁H₂₉NO₅S
• Molecular Weight: 407.531
• Mol file: 146324-53-0.mol

Synonyms:

Chemical Property of (Z)-7-((1R,2S,3S,4R,6S)-3-Benzenesulfonylamino-6-hydroxy-bicyclo[2.2.1]hept-2-yl)-hept-5-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-7-((1R,2S,3S,4R,6S)-3-Benzenesulfonylamino-6-hydroxy-bicyclo[2.2.1]hept-2-yl)-hept-5-enoic acid methyl ester

There total 33 articles about (Z)-7-((1R,2S,3S,4R,6S)-3-Benzenesulfonylamino-6-hydroxy-bicyclo[2.2.1]hept-2-yl)-hept-5-enoic acid methyl ester 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:

(Z)-7-[(1R,2S,3S,4R,6S)-3-Benzenesulfonylamino-6-(tert-butyl-diphenyl-silanyloxy)-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester (146324-56-3) → (Z)-7-((1R,2S,3S,4R,6S)-3-Benzenesulfonylamino-6-hydroxy-bicyclo[2.2.1]hept-2-yl)-hept-5-enoic acid methyl ester (146324-53-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 60 ℃;

DOI:10.1248/cpb.39.2842

Reference yield:

(1S,2S,3S,4R)-3-Amino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester (287395-35-1) → (Z)-7-((1R,2S,3S,4R,6R)-3-Benzenesulfonylamino-6-hydroxy-bicyclo[2.2.1]hept-2-yl)-hept-5-enoic acid methyl ester (146324-53-0)

Guidance literature:

Multi-step reaction with 14 steps

1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: LiAlH₄ / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

3: p-toluenesulfonic acid hydrate / CH₂Cl₂ / 1.5 h / Ambient temperature

4: 1.) 9-borabicyclo<3.3.1>nonane (9-BBN), 2.) 6 N NaOH, 30percent H₂O₂ / 1.) THF, room temperature, 1.5 h, 2.) 60 deg C, 1 h

5: dimethylaminopyridine / dimethylformamide / 50 °C

6: AcOH / tetrahydrofuran; H₂O / 50 °C

7: 99 percent / pyridinium chlorochromate (PCC), molecular sieves (type 4 Angstroem) / CH₂Cl₂ / 1 h / Ambient temperature

8: 1.) tert-BuOK / 1.) THF, 0 deg C, 1 h, 2.) THF, 0 deg C, 20 min

9: 90percent HCO₂H / tetrahydrofuran / 1.5 h / Ambient temperature

10: 1.) tert-BuOK / 1.) THF, room temperature, 1 h, 2.) THF, -15 to 0 deg C, 1 h

11: diethyl ether

12: n-Bu₄NF / tetrahydrofuran / 60 °C

13: pyridinium chlorochromate (PCC)

14: NaBH₄

With dmap; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; formic acid; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; toluene-4-sulfonic acid; acetic acid; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1248/cpb.39.2842

Reference yield:

(1S,2S,3S,4R)-3-Amino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester (287395-35-1) → (Z)-7-((1R,2S,3S,4R,6S)-3-Benzenesulfonylamino-6-hydroxy-bicyclo[2.2.1]hept-2-yl)-hept-5-enoic acid methyl ester (146324-53-0)

Guidance literature:

Multi-step reaction with 12 steps

1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: LiAlH₄ / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

3: p-toluenesulfonic acid hydrate / CH₂Cl₂ / 1.5 h / Ambient temperature

4: 1.) 9-borabicyclo<3.3.1>nonane (9-BBN), 2.) 6 N NaOH, 30percent H₂O₂ / 1.) THF, room temperature, 1.5 h, 2.) 60 deg C, 1 h

5: dimethylaminopyridine / dimethylformamide / 50 °C

6: AcOH / tetrahydrofuran; H₂O / 50 °C

7: 99 percent / pyridinium chlorochromate (PCC), molecular sieves (type 4 Angstroem) / CH₂Cl₂ / 1 h / Ambient temperature

8: 1.) tert-BuOK / 1.) THF, 0 deg C, 1 h, 2.) THF, 0 deg C, 20 min

9: 90percent HCO₂H / tetrahydrofuran / 1.5 h / Ambient temperature

10: 1.) tert-BuOK / 1.) THF, room temperature, 1 h, 2.) THF, -15 to 0 deg C, 1 h

11: diethyl ether

12: n-Bu₄NF / tetrahydrofuran / 60 °C

With dmap; sodium hydroxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; formic acid; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; toluene-4-sulfonic acid; acetic acid; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1248/cpb.39.2842

upstream raw materials:

(1S,2S,3S,4R)-3-Amino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

(1S,2S,3S,4R)-3-Isocyanato-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

(1S,2S,3S,4R)-3-carbobenzoxyamino-2-carbomethoxybicyclo<2.2.1>hept-5-ene

(1S,2S,3S,4R)-2-carbomethoxy-3-phenylsulfonylaminobicyclo<2.2.1>hept-5-ene

Downstream raw materials:

(1R,2S,3S,4R,6R)-(5'Z)-7-(6-hydroxy-3-phenylsulfonylaminobicyclo<2.2.1>hept-2-yl)hept-5'-enoic acid

(1R,2S,3S,4R,6S)-(5'Z)-7'-(6-hydroxy-3-phenylsulfonylaminobicyclo<2.2.1>hept-2-yl)hept-5'-enoic acid

Refernces