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

Base Information

Chemical Name:(1R,2S,3S,4R,6S)-(3'Z)-5'-(6-hydroxy-3-phenylsulfonylaminobicyclo<2.2.1>hept-2-yl)pent-3'-enoic acid
CAS No.:139435-10-2
Molecular Formula:C₁₈H₂₃NO₅S
Molecular Weight:365.45
Hs Code.:

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

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

Chemical Property:

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

There total 16 articles about (1R,2S,3S,4R,6S)-(3'Z)-5'-(6-hydroxy-3-phenylsulfonylaminobicyclo<2.2.1>hept-2-yl)pent-3'-enoic 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:

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

: 139435-10-2
(1R,2S,3S,4R,6S)-(3'Z)-5'-(6-hydroxy-3-phenylsulfonylaminobicyclo<2.2.1>hept-2-yl)pent-3'-enoic acid

Guidance literature:: With potassium hydroxide; In methanol; at 40 ℃; for 2h; Yield given;
DOI:10.1248/cpb.39.2842

Reference yield:

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

: 139435-10-2
(1R,2S,3S,4R,6S)-(3'Z)-5'-(6-hydroxy-3-phenylsulfonylaminobicyclo<2.2.1>hept-2-yl)pent-3'-enoic acid

Guidance literature:: Multi-step reaction with 13 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: 1 N KOH / methanol / 2 h / 40 °C

With dmap; potassium hydroxide; 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; 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

: 139435-10-2
(1R,2S,3S,4R,6S)-(3'Z)-5'-(6-hydroxy-3-phenylsulfonylaminobicyclo<2.2.1>hept-2-yl)pent-3'-enoic acid

Guidance literature:: Multi-step reaction with 15 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.) 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: diethyl ether

14: n-Bu₄NF / tetrahydrofuran / 60 °C

15: 1 N KOH / methanol / 2 h / 40 °C

With dmap; potassium hydroxide; 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; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1248/cpb.39.2842