(1R,2S,3S,4R,6S)-(6-hydroxy-3-phenylsulfonylaminobicyclo<2.2.1>hept-2-yl)propionic acid

Base Information

Chemical Name:(1R,2S,3S,4R,6S)-(6-hydroxy-3-phenylsulfonylaminobicyclo<2.2.1>hept-2-yl)propionic acid
CAS No.:139435-14-6
Molecular Formula:C₁₆H₂₁NO₅S
Molecular Weight:339.412
Hs Code.:

Synonyms:

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Chemical Property of (1R,2S,3S,4R,6S)-(6-hydroxy-3-phenylsulfonylaminobicyclo<2.2.1>hept-2-yl)propionic acid

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Technology Process of (1R,2S,3S,4R,6S)-(6-hydroxy-3-phenylsulfonylaminobicyclo<2.2.1>hept-2-yl)propionic acid

There total 14 articles about (1R,2S,3S,4R,6S)-(6-hydroxy-3-phenylsulfonylaminobicyclo<2.2.1>hept-2-yl)propionic acid 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:

: 287395-35-1
(1S,2S,3S,4R)-3-Amino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

: 139435-14-6
(1R,2S,3S,4R,6S)-(6-hydroxy-3-phenylsulfonylaminobicyclo<2.2.1>hept-2-yl)propionic acid

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: 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.) NaH / 1.) THF, -5 deg C, 35 min, 2.) THF, room temperature, 1 h

9: H₂ / 10percent Pd/C

10: n-Bu₄NF / tetrahydrofuran / 60 °C

11: 1 N KOH / methanol / 2 h / 40 °C

With dmap; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1248/cpb.39.2842

Reference yield:

: 76197-78-9,151292-69-2
(1S,2S,3S,4R)-3-Isocyanato-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

: 139435-14-6
(1R,2S,3S,4R,6S)-(6-hydroxy-3-phenylsulfonylaminobicyclo<2.2.1>hept-2-yl)propionic acid

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: dimethylaminopyridine / dimethylformamide / 50 °C

8: AcOH / tetrahydrofuran; H₂O / 50 °C

9: 99 percent / pyridinium chlorochromate (PCC), molecular sieves (type 4 Angstroem) / CH₂Cl₂ / 1 h / Ambient temperature

10: 1.) NaH / 1.) THF, -5 deg C, 35 min, 2.) THF, room temperature, 1 h

11: H₂ / 10percent Pd/C

12: n-Bu₄NF / tetrahydrofuran / 60 °C

13: 1 N KOH / methanol / 2 h / 40 °C

With dmap; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; pyridinium chlorochromate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; 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

: 139435-14-6
(1R,2S,3S,4R,6S)-(6-hydroxy-3-phenylsulfonylaminobicyclo<2.2.1>hept-2-yl)propionic acid

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: dimethylaminopyridine / dimethylformamide / 50 °C

4: AcOH / tetrahydrofuran; H₂O / 50 °C

5: 99 percent / pyridinium chlorochromate (PCC), molecular sieves (type 4 Angstroem) / CH₂Cl₂ / 1 h / Ambient temperature

6: 1.) NaH / 1.) THF, -5 deg C, 35 min, 2.) THF, room temperature, 1 h

7: H₂ / 10percent Pd/C

8: n-Bu₄NF / tetrahydrofuran / 60 °C

9: 1 N KOH / methanol / 2 h / 40 °C

With dmap; potassium hydroxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; acetic acid; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1248/cpb.39.2842