dl-methyl (1α,2α,3β,5α)-7-<6,6-dimethyl-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hex-2-yl>-5(Z)-heptenoate

Base Information

Chemical Name:dl-methyl (1α,2α,3β,5α)-7-<6,6-dimethyl-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hex-2-yl>-5(Z)-heptenoate
CAS No.:123490-04-0
Molecular Formula:C₂₂H₃₁NO₄S
Molecular Weight:405.558
Hs Code.:

Synonyms:

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Chemical Property of dl-methyl (1α,2α,3β,5α)-7-<6,6-dimethyl-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hex-2-yl>-5(Z)-heptenoate

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Technology Process of dl-methyl (1α,2α,3β,5α)-7-<6,6-dimethyl-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hex-2-yl>-5(Z)-heptenoate

There total 8 articles about dl-methyl (1α,2α,3β,5α)-7-<6,6-dimethyl-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hex-2-yl>-5(Z)-heptenoate 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:

: 112918-39-5,123539-09-3,123539-10-6
dl-(1α,2α,5α)-6,6-dimethyl-3-(hydroxyimino)-2-<2-(triphenylmethoxy)ethyl>bicyclo<3.1.0>hexane

: 123490-04-0
dl-methyl (1α,2α,3β,5α)-7-<6,6-dimethyl-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hex-2-yl>-5(Z)-heptenoate

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) diphenyl disulfide, n-Bu₃P, 2.) sodium cyanoborohydride, acetic acid / 1.) THF, RT, 1 h, 2.) -70 deg C, 10 min

2: Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

3: 80percent aq. AcOH / 15 h / Heating

4: oxalyl chloride/DMSO / CH₂Cl₂ / 0.25 h / -60 °C

5: 1.) sodium (methylsulfinyl)methide, 2.) / 1.) DMSO, RT, 20 min, 2.) RT, 2 h

6: diethyl ether; CH₂Cl₂ / 0 °C

With oxalyl dichloride; tributylphosphine; dimsylsodium; sodium cyanoborohydride; acetic acid; dimethyl sulfoxide; triethylamine; diphenyldisulfane; In diethyl ether; dichloromethane;
DOI:10.1021/jm00163a038

Reference yield:

: 112918-30-6
dl-(1α,2α,3α,5α)-3-acetoxy-6,6-dimethyl-2-<2-(triphenylmethoxy)ethyl>bicyclo<3.1.0>hexane

: 123490-04-0
dl-methyl (1α,2α,3β,5α)-7-<6,6-dimethyl-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hex-2-yl>-5(Z)-heptenoate

Guidance literature:: Multi-step reaction with 9 steps

1: 2 N aq. NaOH / methanol; tetrahydrofuran / 3 h / Heating

2: 99 percent / oxalyl chloride/DMSO / CH₂Cl₂ / 0.33 h / -60 °C

3: KOH, NH₂OH*HCl / methanol / 3 h / Ambient temperature

4: 1.) diphenyl disulfide, n-Bu₃P, 2.) sodium cyanoborohydride, acetic acid / 1.) THF, RT, 1 h, 2.) -70 deg C, 10 min

5: Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

6: 80percent aq. AcOH / 15 h / Heating

7: oxalyl chloride/DMSO / CH₂Cl₂ / 0.25 h / -60 °C

8: 1.) sodium (methylsulfinyl)methide, 2.) / 1.) DMSO, RT, 20 min, 2.) RT, 2 h

9: diethyl ether; CH₂Cl₂ / 0 °C

With potassium hydroxide; sodium hydroxide; oxalyl dichloride; tributylphosphine; dimsylsodium; hydroxylamine hydrochloride; sodium cyanoborohydride; acetic acid; dimethyl sulfoxide; triethylamine; diphenyldisulfane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1021/jm00163a038

Reference yield:

: 112917-45-0
dl-(1α,2α,3β,5α)-6,6-dimethyl-2-(hydroxyethyl)-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hexane

: 123490-04-0
dl-methyl (1α,2α,3β,5α)-7-<6,6-dimethyl-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hex-2-yl>-5(Z)-heptenoate

Guidance literature:: Multi-step reaction with 3 steps

1: oxalyl chloride/DMSO / CH₂Cl₂ / 0.25 h / -60 °C

2: 1.) sodium (methylsulfinyl)methide, 2.) / 1.) DMSO, RT, 20 min, 2.) RT, 2 h

3: diethyl ether; CH₂Cl₂ / 0 °C

With oxalyl dichloride; dimsylsodium; dimethyl sulfoxide; In diethyl ether; dichloromethane;
DOI:10.1021/jm00163a038