methyl (5Z)-7-((1R,2R,3S,5S)-2-(p-nitrophenyl sulfonylamino)-6,6-dimethylbicyclo<3.1.1>hept-3-yl)hept-5-enoate

Base Information

Chemical Name:methyl (5Z)-7-((1R,2R,3S,5S)-2-(p-nitrophenyl sulfonylamino)-6,6-dimethylbicyclo<3.1.1>hept-3-yl)hept-5-enoate
CAS No.:120632-47-5
Molecular Formula:C₂₃H₃₂N₂O₆S
Molecular Weight:464.583
Hs Code.:

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

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Chemical Property of methyl (5Z)-7-((1R,2R,3S,5S)-2-(p-nitrophenyl sulfonylamino)-6,6-dimethylbicyclo<3.1.1>hept-3-yl)hept-5-enoate

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Technology Process of methyl (5Z)-7-((1R,2R,3S,5S)-2-(p-nitrophenyl sulfonylamino)-6,6-dimethylbicyclo<3.1.1>hept-3-yl)hept-5-enoate

There total 11 articles about methyl (5Z)-7-((1R,2R,3S,5S)-2-(p-nitrophenyl sulfonylamino)-6,6-dimethylbicyclo<3.1.1>hept-3-yl)hept-5-enoate 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: 97.6%

: 197069-37-7
(1R,2R,3S,5S)-(5Z)-7-(2-amino-6,6-dimethylbicyclo[3.1.1]hept-3-yl)-hept-5-enoic acid methyl ester

: 98-74-8
4-Nitrobenzenesulfonyl chloride

: 120632-47-5
methyl (5Z)-7-((1R,2R,3S,5S)-2-(p-nitrophenyl sulfonylamino)-6,6-dimethylbicyclo<3.1.1>hept-3-yl)hept-5-enoate

Guidance literature:: With triethylamine; In dichloromethane; for 1h; Ambient temperature;
DOI:10.1248/cpb.37.1524

Reference yield:

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

: 120632-47-5
methyl (5Z)-7-((1R,2R,3S,5S)-2-(p-nitrophenyl sulfonylamino)-6,6-dimethylbicyclo<3.1.1>hept-3-yl)hept-5-enoate

Guidance literature:: Multi-step reaction with 7 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: 97.6 percent / triethylamine / CH₂Cl₂ / 1 h / Ambient temperature

With potassium dichromate; sodium azide; sulfuric acid; chloroformic acid ethyl ester; sodium hydride; triethylamine; trifluoroacetic acid; In 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

: 120632-47-5
methyl (5Z)-7-((1R,2R,3S,5S)-2-(p-nitrophenyl sulfonylamino)-6,6-dimethylbicyclo<3.1.1>hept-3-yl)hept-5-enoate

Guidance literature:: Multi-step reaction with 5 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: 97.6 percent / triethylamine / CH₂Cl₂ / 1 h / Ambient temperature

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