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

Base Information

• Chemical Name: dl-(1β,2α,3β,5β)-7-<6,6-dimethyl-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hex-2-yl>-5(Z)-heptenoic acid
• CAS No.: 112917-60-9
• Molecular Formula: C₂₁H₂₉NO₄S
• Molecular Weight: 391.532
• Mol file: 112917-60-9.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about dl-(1β,2α,3β,5β)-7-<6,6-dimethyl-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hex-2-yl>-5(Z)-heptenoic 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:

dl-(1α,2α,3α,5α)-3-acetoxy-6,6-dimethyl-2-<2-(triphenylmethoxy)ethyl>bicyclo<3.1.0>hexane (112918-30-6) → dl-(1β,2α,3β,5β)-7-<6,6-dimethyl-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hex-2-yl>-5(Z)-heptenoic acid (112917-60-9)

Guidance literature:

Multi-step reaction with 11 steps

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

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

3: 75 percent / t-BuOK / dimethylformamide / 8 h / Ambient temperature

4: 60 percent / lithium tri-tert-butoxyaluminiumhydride / tetrahydrofuran / 2.5 h / Ambient temperature

5: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

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

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

8: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

9: 1 N aq. HCl / tetrahydrofuran; methanol / 2 h / 45 °C

10: oxalyl chloride/DMSO / CH₂Cl₂ / 15 h / -60 °C

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

With hydrogenchloride; sodium hydroxide; sodium azide; oxalyl dichloride; dimsylsodium; potassium tert-butylate; water; dimethyl sulfoxide; lithium tri-t-butoxyaluminum hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00163a038

Reference yield:

dl-(1β,2α,3β,5β)-3-azido-6,6-dimethyl-2-<2-(triphenylmethoxy)ethyl>bicyclo<3.1.0>hexane (112918-34-0) → dl-(1β,2α,3β,5β)-7-<6,6-dimethyl-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hex-2-yl>-5(Z)-heptenoic acid (112917-60-9)

Guidance literature:

Multi-step reaction with 5 steps

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

2: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: 1 N aq. HCl / tetrahydrofuran; methanol / 2 h / 45 °C

4: oxalyl chloride/DMSO / CH₂Cl₂ / 15 h / -60 °C

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

With hydrogenchloride; oxalyl dichloride; dimsylsodium; water; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00163a038

Reference yield:

(1S,2S,3S,5S)-6,6-Dimethyl-2-(2-trityloxy-ethyl)-bicyclo[3.1.0]hex-3-ylamine (112918-35-1) → dl-(1β,2α,3β,5β)-7-<6,6-dimethyl-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hex-2-yl>-5(Z)-heptenoic acid (112917-60-9)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

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

3: oxalyl chloride/DMSO / CH₂Cl₂ / 15 h / -60 °C

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

With hydrogenchloride; oxalyl dichloride; dimsylsodium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00163a038

upstream raw materials:

(4-carboxybutyl)triphenylphosphonium bromide

dl-(1β,2α,3β,5β)-6,6-dimethyl-2-(formylmethyl)-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hexane

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

dl-(1β,2α,3β,5β)-3-azido-6,6-dimethyl-2-<2-(triphenylmethoxy)ethyl>bicyclo<3.1.0>hexane

Downstream raw materials:

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

Refernces