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

Base Information

• Chemical Name: (Z)-7-[(1S,2S,3R,4S,5R)-3-Benzenesulfonylamino-5-(tert-butyl-diphenyl-silanyloxy)-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester
• CAS No.: 146344-96-9
• Molecular Formula: C₃₇H₄₇NO₅SSi
• Molecular Weight: 645.935
• Mol file: 146344-96-9.mol

Synonyms:

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

There total 13 articles about (Z)-7-[(1S,2S,3R,4S,5R)-3-Benzenesulfonylamino-5-(tert-butyl-diphenyl-silanyloxy)-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:

(1S,2S,3S,4R)-3-Amino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester (287395-35-1) → (Z)-7-[(1S,2S,3R,4S,5R)-3-Benzenesulfonylamino-5-(tert-butyl-diphenyl-silanyloxy)-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester (146344-96-9)

Guidance literature:

Multi-step reaction with 11 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: 2.15 g / dimethylaminopyridine / dimethylformamide / 50 °C

6: AcOH / tetrahydrofuran; H₂O / 50 °C

7: 94 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: 647 mg / diethyl ether

With dmap; sodium hydroxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; formic acid; 4 A molecular sieve; potassium tert-butylate; 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-Isocyanato-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester (76197-78-9,151292-69-2) → (Z)-7-[(1S,2S,3R,4S,5R)-3-Benzenesulfonylamino-5-(tert-butyl-diphenyl-silanyloxy)-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester (146344-96-9)

Guidance literature:

Multi-step reaction with 13 steps

1: Et₃N / benzene / 1 h / Heating

2: CF₃CO₂H / various solvent(s) / 6 h / 45 °C

3: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

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

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

6: 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

7: 2.15 g / dimethylaminopyridine / dimethylformamide / 50 °C

8: AcOH / tetrahydrofuran; H₂O / 50 °C

9: 94 percent / pyridinium chlorochromate (PCC), molecular sieves (type 4 Angstroem) / CH₂Cl₂ / 1 h / Ambient temperature

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

11: 90percent HCO₂H / tetrahydrofuran / 1.5 h / Ambient temperature

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

13: 647 mg / diethyl ether

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

DOI:10.1248/cpb.39.2842

Reference yield:

N-((1R,2S,3S,4S)-3-Hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-benzenesulfonamide → (Z)-7-[(1S,2S,3R,4S,5R)-3-Benzenesulfonylamino-5-(tert-butyl-diphenyl-silanyloxy)-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester (146344-96-9)

Guidance literature:

Multi-step reaction with 9 steps

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

2: 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

3: 2.15 g / dimethylaminopyridine / dimethylformamide / 50 °C

4: AcOH / tetrahydrofuran; H₂O / 50 °C

5: 94 percent / pyridinium chlorochromate (PCC), molecular sieves (type 4 Angstroem) / CH₂Cl₂ / 1 h / Ambient temperature

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

7: 90percent HCO₂H / tetrahydrofuran / 1.5 h / Ambient temperature

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

9: 647 mg / diethyl ether

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

DOI:10.1248/cpb.39.2842

upstream raw materials:

diazomethane

(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

Downstream raw materials:

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

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

Refernces