(Z)-7-[(1R,2R,3S,5S)-6,6-Dimethyl-2-(toluene-4-sulfonylamino)-bicyclo[3.1.1]hept-3-yl]-hept-5-enoic acid

Base Information

Chemical Name:(Z)-7-[(1R,2R,3S,5S)-6,6-Dimethyl-2-(toluene-4-sulfonylamino)-bicyclo[3.1.1]hept-3-yl]-hept-5-enoic acid
CAS No.:120632-67-9
Molecular Formula:C₂₃H₃₃NO₄S
Molecular Weight:419.585
Hs Code.:

Synonyms:(Z)-7-[(1R,2R,3S,5S)-6,6-Dimethyl-2-(toluene-4-sulfonylamino)-bicyclo[3.1.1]hept-3-yl]-hept-5-enoic acid

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Chemical Property of (Z)-7-[(1R,2R,3S,5S)-6,6-Dimethyl-2-(toluene-4-sulfonylamino)-bicyclo[3.1.1]hept-3-yl]-hept-5-enoic acid

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Technology Process of (Z)-7-[(1R,2R,3S,5S)-6,6-Dimethyl-2-(toluene-4-sulfonylamino)-bicyclo[3.1.1]hept-3-yl]-hept-5-enoic acid

There total 13 articles about (Z)-7-[(1R,2R,3S,5S)-6,6-Dimethyl-2-(toluene-4-sulfonylamino)-bicyclo[3.1.1]hept-3-yl]-hept-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: 90.0%

: 120643-99-4
methyl (5Z)-7-((1R,2R,3S,5S)-2-(p-methylphenyl sulfonylamino)-6,6-dimethylbicyclo<3.1.1>hept-3-yl)hept-5-enoate

: 120632-67-9
(Z)-7-[(1R,2R,3S,5S)-6,6-Dimethyl-2-(toluene-4-sulfonylamino)-bicyclo[3.1.1]hept-3-yl]-hept-5-enoic acid

Guidance literature:: With sodium hydroxide; In methanol; for 2h; Ambient temperature;
DOI:10.1248/cpb.37.1524

Reference yield:

: 17814-85-6
(4-carboxybutyl)triphenylphosphonium bromide

: 120632-67-9
(Z)-7-[(1R,2R,3S,5S)-6,6-Dimethyl-2-(toluene-4-sulfonylamino)-bicyclo[3.1.1]hept-3-yl]-hept-5-enoic acid

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) 60percent sodium hydride / 1.) DMSO, room temperature, 2.) ether, 10 min,

2: 93.4 percent / K₂Cr₂O₇, H₂SO₄ / acetone / 1 h / 0 °C

3: 1.) ethyl chloroformate, 2.) sodium azide / 1.) acetone, 0 deg C, 1 h, 2.) acetone, water, 0 deg C, 1 h,

4: benzene / 0.5 h / Heating

5: 72 h / Heating

6: trifluoroacetic acid / CH₂Cl₂ / 0.5 h / Ambient temperature

7: 80.8 percent / triethylamine / CH₂Cl₂ / 1 h / Ambient temperature

8: 90 percent / 10percent aqueous sodium hydroxide / methanol / 2 h / Ambient temperature

With potassium dichromate; sodium hydroxide; sodium azide; sulfuric acid; chloroformic acid ethyl ester; sodium hydride; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; acetone; benzene;
DOI:10.1248/cpb.37.1524

Reference yield:

: 126264-14-0
(+)-2-((1R,2R,3R,5S)-2-tert-butoxycarbonilamino-6,6-dimethylbicyclo<3.1.1>hept-3-yl)ethanol

: 120632-67-9
(Z)-7-[(1R,2R,3S,5S)-6,6-Dimethyl-2-(toluene-4-sulfonylamino)-bicyclo[3.1.1]hept-3-yl]-hept-5-enoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: DMSO, oxalyl chloride, triethyl amine / CH₂Cl₂

2: 1.) potassium tert-butoxide / 1.) THF, room temperature, 1 h, 2.) THF, 0 deg C, 1 h,

3: diethyl ether / 0.17 h

4: trifluoroacetic acid / CH₂Cl₂ / 0.5 h / Ambient temperature

5: 80.8 percent / triethylamine / CH₂Cl₂ / 1 h / Ambient temperature

6: 90 percent / 10percent aqueous sodium hydroxide / methanol / 2 h / Ambient temperature

With sodium hydroxide; oxalyl dichloride; potassium tert-butylate; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In methanol; diethyl ether; dichloromethane;
DOI:10.1248/cpb.37.1524