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

Base Information

Chemical Name:dl-methyl (1α,2α,3α,5α)-7-<3-<(phenylsulfonyl)amino>-6-oxabicyclo<3.1.0>hex-2-yl>-5(Z)-heptenoate
CAS No.:112967-18-7
Molecular Formula:C₁₉H₂₅NO₅S
Molecular Weight:379.477
Hs Code.:

Synonyms:

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

Chemical Property:

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

There total 18 articles about dl-methyl (1α,2α,3α,5α)-7-<3-<(phenylsulfonyl)amino>-6-oxabicyclo<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:

: 49826-08-6,54483-54-4,54483-55-5,75331-67-8
1-hydroxy-2-(2-hydroxyethyl)cyclopent-3-ene

: 112917-64-3,112967-18-7,112967-20-1,112968-64-6
dl-(1α,2α,3β,5α)-7-<3-<(phenylsulfonyl)amino>-6-oxabicyclo<3.1.0>hex-2-yl>-5(Z)-heptenoic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 96 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 h / Ambient temperature

2: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: NaN₃ / dimethylformamide / 5 h / 75 °C

4: 1.) Ph₃P, 2.) H₂O / 1.) RT, 15 h, 2.) a.) 45 deg C, 2 h, b.) reflux, 1 h

5: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

6: 99 percent / 1 N aq. HCl / tetrahydrofuran; methanol / 2 h / 45 °C

7: 43.4 percent / 80percent 3-chloroperbenzoic acid / CH₂Cl₂ / 15 h / 0 °C

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

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

10: diethyl ether; CH₂Cl₂ / 0 °C

With hydrogenchloride; dmap; sodium azide; oxalyl dichloride; dimsylsodium; water; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00163a038

Reference yield:

: 49826-08-6,54483-54-4,54483-55-5,75331-67-8
1-hydroxy-2-(2-hydroxyethyl)cyclopent-3-ene

: 112967-18-7
dl-methyl (1α,2α,3α,5α)-7-<3-<(phenylsulfonyl)amino>-6-oxabicyclo<3.1.0>hex-2-yl>-5(Z)-heptenoate

Guidance literature:: Multi-step reaction with 12 steps

1: 96 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 h / Ambient temperature

2: 40.9 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 0.25 h / Ambient temperature

3: 95 percent / Na₂CO₃ / tetrahydrofuran; H₂O / 5 h / Heating

4: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

5: NaN₃ / dimethylformamide / 5 h / 75 °C

6: 1.) Ph₃P, 2.) H₂O / 1.) RT, 15 h, 2.) a.) 45 deg C, 2 h, b.) reflux, 1 h

7: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

8: 1 N aq. HCl / tetrahydrofuran; methanol / 2 h / 45 °C

9: 64 percent / oxalyl chloride/DMSO / CH₂Cl₂ / 0.25 h / -60 °C

10: 27 percent / 80percent 3-chloroperbenzoic acid / CH₂Cl₂ / 3 h / Ambient temperature

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

12: diethyl ether; CH₂Cl₂ / 0 °C

With hydrogenchloride; dmap; sodium azide; oxalyl dichloride; dimsylsodium; water; sodium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm00163a038

Reference yield:

: 113007-97-9
dl-(1α,5α)-2-(phenylsulfonyl)-3-hydroxy-2-azabicyclo<3.3.0>oct-6-ene

: 112967-18-7
dl-methyl (1α,2α,3α,5α)-7-<3-<(phenylsulfonyl)amino>-6-oxabicyclo<3.1.0>hex-2-yl>-5(Z)-heptenoate

Guidance literature:: Multi-step reaction with 3 steps

1: 27 percent / 80percent 3-chloroperbenzoic acid / CH₂Cl₂ / 3 h / Ambient temperature

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

3: diethyl ether; CH₂Cl₂ / 0 °C

With dimsylsodium; 3-chloro-benzenecarboperoxoic acid; In diethyl ether; dichloromethane;
DOI:10.1021/jm00163a038