(5Z)-6-<(1R,2R,3R,4S)-3-bicyclo<2.2.1>heptan-2-yl>hex-5-enoic acid

Base Information

Chemical Name:(5Z)-6-<(1R,2R,3R,4S)-3-bicyclo<2.2.1>heptan-2-yl>hex-5-enoic acid
CAS No.:143120-15-4
Molecular Formula:C₂₂H₃₀BrNO₅S
Molecular Weight:500.454
Hs Code.:

(5Z)-6-<(1R,2R,3R,4S)-3-<N,N-(4-bromobenzenesulfonyl)methoxymethylaminomethyl>bicyclo<2.2.1>heptan-2-yl>hex-5-enoic acid

Synonyms:(5Z)-6-<(1R,2R,3R,4S)-3-bicyclo<2.2.1>heptan-2-yl>hex-5-enoic acid

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Chemical Property of (5Z)-6-<(1R,2R,3R,4S)-3-bicyclo<2.2.1>heptan-2-yl>hex-5-enoic acid

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Technology Process of (5Z)-6-<(1R,2R,3R,4S)-3-bicyclo<2.2.1>heptan-2-yl>hex-5-enoic acid

There total 12 articles about (5Z)-6-<(1R,2R,3R,4S)-3-bicyclo<2.2.1>heptan-2-yl>hex-5-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:

: 941567-71-1,448922-61-0
(1R,2S,3R,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dimethanol

: 143120-15-4
(5Z)-6-<(1R,2R,3R,4S)-3-bicyclo<2.2.1>heptan-2-yl>hex-5-enoic acid

Guidance literature:: Multi-step reaction with 12 steps

1: CH₂Cl₂ / 3 h / Ambient temperature; lipase AY from Candida rugosa

2: 99 percent / pyridine / 12 h / Ambient temperature

3: 100 percent / H₂ / 5percent Pd/C / ethanol / Ambient temperature

4: 50 percent / NaN₃ / dimethylformamide / 3 h / 100 °C

5: 93 percent / CH₃ONa / methanol / 3 h / Ambient temperature

6: 97 percent / H₂ / 5percent Pd/C / ethanol / Ambient temperature

7: 87 percent / Et₃N / toluene / 12 h / Ambient temperature

8: 94 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

9: 30 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 12 h / Ambient temperature

10: 80 percent / CH₃ONa / methanol / 2 h / Ambient temperature

11: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, -78 - 0 deg C, 1 h

12: 1.) tert-BuOK / 1.) THF, RT, 1 h, 2.) THF, 0 deg C, 1 h

With pyridine; sodium azide; oxalyl dichloride; potassium tert-butylate; hydrogen; sodium methylate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1248/cpb.40.2610

Reference yield:

: 131222-96-3
(-)-(2S,3R)-cis-3-(azidomethyl)-2-(hydroxymethyl)bicyclo<2.2.1>heptane

: 143120-15-4
(5Z)-6-<(1R,2R,3R,4S)-3-bicyclo<2.2.1>heptan-2-yl>hex-5-enoic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 97 percent / H₂ / 5percent Pd/C / ethanol / Ambient temperature

2: 87 percent / Et₃N / toluene / 12 h / Ambient temperature

3: 94 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

4: 30 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 12 h / Ambient temperature

5: 80 percent / CH₃ONa / methanol / 2 h / Ambient temperature

6: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, -78 - 0 deg C, 1 h

7: 1.) tert-BuOK / 1.) THF, RT, 1 h, 2.) THF, 0 deg C, 1 h

With oxalyl dichloride; potassium tert-butylate; hydrogen; sodium methylate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; ethanol; dichloromethane; toluene;
DOI:10.1248/cpb.40.2610

Reference yield:

: 131222-93-0
(-)-(2S,3R)-cis-3-(tosyloxymethyl)-2-(acetoxymethyl)bicyclo<2.2.1>hept-5-ene

: 143120-15-4
(5Z)-6-<(1R,2R,3R,4S)-3-bicyclo<2.2.1>heptan-2-yl>hex-5-enoic acid

Guidance literature:: Multi-step reaction with 10 steps

1: 100 percent / H₂ / 5percent Pd/C / ethanol / Ambient temperature

2: 50 percent / NaN₃ / dimethylformamide / 3 h / 100 °C

3: 93 percent / CH₃ONa / methanol / 3 h / Ambient temperature

4: 97 percent / H₂ / 5percent Pd/C / ethanol / Ambient temperature

5: 87 percent / Et₃N / toluene / 12 h / Ambient temperature

6: 94 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

7: 30 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 12 h / Ambient temperature

8: 80 percent / CH₃ONa / methanol / 2 h / Ambient temperature

9: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, -78 - 0 deg C, 1 h

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

With sodium azide; oxalyl dichloride; potassium tert-butylate; hydrogen; sodium methylate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1248/cpb.40.2610