Product Name

  • Name

    (1S,5R,6S)-Ethyl 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate

  • EINECS 429-020-1
  • CAS No. 204254-96-6
  • Article Data7
  • CAS DataBase
  • Density 1.09 g/cm3
  • Solubility
  • Melting Point 56-57 °C
  • Formula C14H22O4
  • Boiling Point 336.495 °C at 760 mmHg
  • Molecular Weight 254.326
  • Flash Point 145.075 °C
  • Transport Information
  • Appearance White to off-white solid
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 204254-96-6 ((1S,5R,6S)-Ethyl 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate)
  • Hazard Symbols
  • Synonyms [1S-(1a,5b,6a)]-5-(1-Ethylpropoxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester;Ethyl(3r,4s,5s)-4,5-Epoxy-3-(1-Ethyl-Propoxy)-Cyclohex-1-Ene-1-Carboxylate;
  • PSA 48.06000
  • LogP 2.22080

Synthetic route

ethyl (3R,4R,5R)-3-(1-ethyl-propoxy)-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate
204254-92-2

ethyl (3R,4R,5R)-3-(1-ethyl-propoxy)-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethanol; water at 60℃; for 2h;
With potassium hydrogencarbonate In ethanol at 60℃; for 1h;2 g
With sodium hydrogencarbonate In ethanol at 60 - 65℃; for 1.5h; Inert atmosphere; Industrial scale; Large scale;1.55 kg
ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate
204254-90-0

ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; potassium hydrogencarbonate 1.) dichloromethane, -20 - -10 deg C, 0.2 h, 2.) ethanol, water, 55-65 deg C, 1 h; Yield given. Multistep reaction;
Stage #1: ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate With trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex In dichloromethane at -30 - -20℃; for 1h;
Stage #2: With sodium hydrogencarbonate In dichloromethane; water at 20℃; for 12h;
Stage #3: With potassium hydrogencarbonate In ethanol; water at 55 - 65℃; for 2h;
ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate
204254-84-2

ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / perchloric acid
2: 1.) BH3-SMe2, trimethylsilyl trifluoromethanesulfonate, 2.) potassium hydroden carbonate / 1.) dichloromethane, -20 - -10 deg C, 0.2 h, 2.) ethanol, water, 55-65 deg C, 1 h
View Scheme
Multi-step reaction with 2 steps
1.1: perchloric acid / 18 h
2.1: dimethylsulfide borane complex; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -30 - -20 °C
2.2: 12 h / 20 °C
2.3: 2 h / 55 - 65 °C
View Scheme
ethyl (3aR,5S,7R,7aR)-5-hydroxy-7-methanesulfonyloxy-2,2-dimethylhexahydrobenzo[1,3]dioxole-5-carboxylate
204254-81-9

ethyl (3aR,5S,7R,7aR)-5-hydroxy-7-methanesulfonyloxy-2,2-dimethylhexahydrobenzo[1,3]dioxole-5-carboxylate

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: pyridine; sulfuryl dichloride / dichloromethane / -30 - -20 °C
2.1: perchloric acid / 18 h
3.1: dimethylsulfide borane complex; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -30 - -20 °C
3.2: 12 h / 20 °C
3.3: 2 h / 55 - 65 °C
View Scheme
D-(-)-quinic acid
77-95-2

D-(-)-quinic acid

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: toluene-4-sulfonic acid / acetone / 2 h / Reflux; Large scale
2.1: ethanol / 2 h / 20 °C
2.2: 1 h / 0 - 10 °C
3.1: pyridine; sulfuryl dichloride / dichloromethane / -30 - -20 °C
4.1: perchloric acid / 18 h
5.1: dimethylsulfide borane complex; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -30 - -20 °C
5.2: 12 h / 20 °C
5.3: 2 h / 55 - 65 °C
View Scheme
2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: toluene-4-sulfonic acid / acetone / 2 h / Reflux; Large scale
2.1: ethanol / 2 h / 20 °C
2.2: 1 h / 0 - 10 °C
3.1: pyridine; sulfuryl dichloride / dichloromethane / -30 - -20 °C
4.1: perchloric acid / 18 h
5.1: dimethylsulfide borane complex; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -30 - -20 °C
5.2: 12 h / 20 °C
5.3: 2 h / 55 - 65 °C
View Scheme
(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone
32384-42-2

(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: ethanol / 2 h / 20 °C
1.2: 1 h / 0 - 10 °C
2.1: pyridine; sulfuryl dichloride / dichloromethane / -30 - -20 °C
3.1: perchloric acid / 18 h
4.1: dimethylsulfide borane complex; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -30 - -20 °C
4.2: 12 h / 20 °C
4.3: 2 h / 55 - 65 °C
View Scheme
1-amino-2-propene
107-11-9

1-amino-2-propene

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

ethyl (3R,4S,5R)-5-N-allyllamino-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate
312904-11-3

ethyl (3R,4S,5R)-5-N-allyllamino-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate

Conditions
ConditionsYield
With magnesium bromide In acetonitrile at 55℃; for 16h;97%
tert-butylamine
75-64-9

tert-butylamine

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

A

C14H20O3
1151665-78-9

C14H20O3

B

C14H23ClO4

C14H23ClO4

C

(3R,4S,5R)-[5-(tert-butylamino)-4-hydroxy-3-(pent-3-yloxy)]cyclohex-1-ene-1-carboxylic acid ethyl ester
651324-04-8

(3R,4S,5R)-[5-(tert-butylamino)-4-hydroxy-3-(pent-3-yloxy)]cyclohex-1-ene-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: tert-butylamine With magnesium chloride In toluene at 10℃; for 1h;
Stage #2: (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester In toluene at 60℃; for 48h; Temperature; Time;		A 1.65%
B 0.83%
C 95.8%
...Expand
acetonitrile
75-05-8

acetonitrile

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

(3R,4S,5R)-ethyl 5-acetylamino-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate
1443055-47-7

(3R,4S,5R)-ethyl 5-acetylamino-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

Conditions
ConditionsYield
Stage #1: acetonitrile; (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester With boron trifluoride diethyl etherate at 0℃; for 1.16667h;
Stage #2: With water In acetonitrile at 0 - 20℃; for 4h;
Stage #3: With potassium carbonate In acetonitrile at 20℃; for 36h; diastereoselective reaction;		95%
tert-butylamine
75-64-9

tert-butylamine

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

(3R,4S,5R)-[5-(tert-butylamino)-4-hydroxy-3-(pent-3-yloxy)]cyclohex-1-ene-1-carboxylic acid ethyl ester
651324-04-8

(3R,4S,5R)-[5-(tert-butylamino)-4-hydroxy-3-(pent-3-yloxy)]cyclohex-1-ene-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: tert-butylamine; (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester With magnesium chloride In toluene at 50℃; for 23h;
Stage #2: With citric acid		91%
Stage #1: tert-butylamine With magnesium chloride In toluene for 6h;
Stage #2: (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester In toluene at 25 - 50℃; for 20h;		89.7%
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

ethyl-(3R,4S,5R)-5-azido-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

ethyl-(3R,4S,5R)-5-azido-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

Conditions
ConditionsYield
Stage #1: (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester With water; ammonium chloride In ethanol for 0.333333h;
Stage #2: With sodium azide In ethanol at 68℃; for 14h;		90%
With sodium azide; ammonium chloride In ethanol; water at 65 - 75℃; for 8h;86.9%
With sodium azide; ammonium chloride In methanol; water at 65 - 70℃;70%
benzylamine
100-46-9

benzylamine

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

ethyl (3R,4S,5R)-5-N-benzylamino-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate

ethyl (3R,4S,5R)-5-N-benzylamino-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate

Conditions
ConditionsYield
Stage #1: benzylamine With zinc(II) chloride In tetrahydrofuran for 1h;
Stage #2: (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester In tetrahydrofuran at 50℃; for 24h; Reagent/catalyst; Temperature;		89%
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

ethyl (3R,4S,5R)-5-amino-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate
312904-12-4

ethyl (3R,4S,5R)-5-amino-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 97 percent / MgBr2*OEt2 / acetonitrile; various solvent(s) / 16 h / 55 °C
2.1: ethanolamine; Pd/C / ethanol / 3 h / Heating
2.2: 77 percent / H2SO4
View Scheme
Multi-step reaction with 2 steps
1.1: zinc(II) chloride / tetrahydrofuran / 1 h
1.2: 24 h / 50 °C
2.1: hydrogen; palladium on activated charcoal / isopropyl alcohol; acetonitrile / 6 h / 60 °C / 760.05 Torr
View Scheme
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

ethyl (3R,4R,5S)-5-N-allylamino-4-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate
312904-15-7

ethyl (3R,4R,5S)-5-N-allylamino-4-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 97 percent / MgBr2*OEt2 / acetonitrile; various solvent(s) / 16 h / 55 °C
2.1: ethanolamine; Pd/C / ethanol / 3 h / Heating
2.2: 77 percent / H2SO4
3.1: various solvent(s)
4.1: Et3N / various solvent(s)
5.1: various solvent(s) / 15 h / 111 - 112 °C / 2625.21 - 3375.27 Torr
View Scheme
Multi-step reaction with 5 steps
1.1: MgBr2*OEt2 / acetonitrile; various solvent(s) / Heating
1.2: H2NCH2CH2OH / Pd/C / ethanol / 3 h / Heating
2.1: 6 h / 100 °C / 750.08 - 3750.38 Torr
3.1: Et3N / ethyl acetate / 0 - 20 °C
4.1: MeSO3H / ethanol / 2.67 h / Heating
5.1: ethyl acetate / 6 h / 112 °C / 750.08 - 4500.45 Torr
View Scheme
Multi-step reaction with 5 steps
1.1: MgBr2*OEt2 / acetonitrile; various solvent(s) / Heating
1.2: HOCH2CH2OH / Pd/C / ethanol / Heating
2.1: 6 h / 100 °C / 750.08 - 3750.38 Torr
3.1: Et3N / ethyl acetate / 0 - 20 °C
4.1: MeSO3H / ethanol / 2.67 h / Heating
5.1: ethyl acetate / 6 h / 112 °C / 750.08 - 4500.45 Torr
View Scheme
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

ethyl (3R,4S,5R)-5-N-benzylideneamino-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate
332047-17-3

ethyl (3R,4S,5R)-5-N-benzylideneamino-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 97 percent / MgBr2*OEt2 / acetonitrile; various solvent(s) / 16 h / 55 °C
2.1: ethanolamine; Pd/C / ethanol / 3 h / Heating
2.2: 77 percent / H2SO4
3.1: various solvent(s)
View Scheme
Multi-step reaction with 2 steps
1.1: MgBr2*OEt2 / acetonitrile; various solvent(s) / Heating
1.2: H2NCH2CH2OH / Pd/C / ethanol / 3 h / Heating
2.1: 100 percent / toluene / 0.5 h / 110 °C
View Scheme
Multi-step reaction with 2 steps
1.1: MgBr2*OEt2 / acetonitrile; various solvent(s) / Heating
1.2: HOCH2CH2OH / Pd/C / ethanol / Heating
2.1: 100 percent / toluene / 0.5 h / 110 °C
View Scheme
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

ethyl (3R,4S,5R)-5-N-benzylideneamino-3-(1-ethylpropoxy)-4-methanesulfonyloxy-1-cyclohexene-1-carboxylate
332047-18-4

ethyl (3R,4S,5R)-5-N-benzylideneamino-3-(1-ethylpropoxy)-4-methanesulfonyloxy-1-cyclohexene-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 97 percent / MgBr2*OEt2 / acetonitrile; various solvent(s) / 16 h / 55 °C
2.1: ethanolamine; Pd/C / ethanol / 3 h / Heating
2.2: 77 percent / H2SO4
3.1: various solvent(s)
4.1: Et3N / various solvent(s)
View Scheme
Multi-step reaction with 3 steps
1.1: MgBr2*OEt2 / acetonitrile; various solvent(s) / Heating
1.2: H2NCH2CH2OH / Pd/C / ethanol / 3 h / Heating
2.1: 100 percent / toluene / 0.5 h / 110 °C
3.1: 94 percent / Et3N / ethyl acetate / 1 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: MgBr2*OEt2 / acetonitrile; various solvent(s) / Heating
1.2: HOCH2CH2OH / Pd/C / ethanol / Heating
2.1: 100 percent / toluene / 0.5 h / 110 °C
3.1: 94 percent / Et3N / ethyl acetate / 1 h / 20 °C
View Scheme
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

ethyl (3R,4R,5S)-4-N-acetylamino-5-N-allylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate
312904-18-0

ethyl (3R,4R,5S)-4-N-acetylamino-5-N-allylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 97 percent / MgBr2*OEt2 / acetonitrile; various solvent(s) / 16 h / 55 °C
2.1: ethanolamine; Pd/C / ethanol / 3 h / Heating
2.2: 77 percent / H2SO4
3.1: various solvent(s)
4.1: Et3N / various solvent(s)
5.1: various solvent(s) / 15 h / 111 - 112 °C / 2625.21 - 3375.27 Torr
6.1: AcOH; MeSO3H / various solvent(s) / 15 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: MgBr2*OEt2 / acetonitrile; various solvent(s) / Heating
1.2: H2NCH2CH2OH / Pd/C / ethanol / 3 h / Heating
2.1: 6 h / 100 °C / 750.08 - 3750.38 Torr
3.1: Et3N / ethyl acetate / 0 - 20 °C
4.1: MeSO3H / ethanol / 2.67 h / Heating
5.1: ethyl acetate / 6 h / 112 °C / 750.08 - 4500.45 Torr
6.1: AcOH; MeSO3H / various solvent(s) / 0 - 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: MgBr2*OEt2 / acetonitrile; various solvent(s) / Heating
1.2: HOCH2CH2OH / Pd/C / ethanol / Heating
2.1: 6 h / 100 °C / 750.08 - 3750.38 Torr
3.1: Et3N / ethyl acetate / 0 - 20 °C
4.1: MeSO3H / ethanol / 2.67 h / Heating
5.1: ethyl acetate / 6 h / 112 °C / 750.08 - 4500.45 Torr
6.1: AcOH; MeSO3H / various solvent(s) / 0 - 20 °C
View Scheme
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

(1R,5R,6R)-{7-(tert-butyl)-5-(pent-3-yloxy)-7-azabicyclo[4.1.0]}hept-3-ene-3-ethyl carboxylate

(1R,5R,6R)-{7-(tert-butyl)-5-(pent-3-yloxy)-7-azabicyclo[4.1.0]}hept-3-ene-3-ethyl carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: MgCl2 / toluene / 23 h / 50 °C
1.2: 91 percent / aq. citric acid
2.1: Et3N / toluene / 5 h / 70 °C
3.1: 93 percent / aq. K2CO3
View Scheme
Multi-step reaction with 2 steps
1.1: magnesium chloride / toluene / 6 h
1.2: 20 h / 25 - 50 °C
2.1: methanesulfonyl chloride / toluene / 1 h / 0 - 10 °C / Inert atmosphere
2.2: 3.5 h / 0 - 70 °C
View Scheme
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

(3R,4S,5R)-5-tert-Butylamino-3-(1-ethyl-propoxy)-4-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester

(3R,4S,5R)-5-tert-Butylamino-3-(1-ethyl-propoxy)-4-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: MgCl2 / toluene / 23 h / 50 °C
1.2: 91 percent / aq. citric acid
2.1: Et3N / toluene / 5 h / 70 °C
View Scheme
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

ethyl (3R,4R,5S)-5-N,N-diallylamino-4-(1,1-dimethylethyl)amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate
651324-06-0

ethyl (3R,4R,5S)-5-N,N-diallylamino-4-(1,1-dimethylethyl)amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: MgCl2 / toluene / 23 h / 50 °C
1.2: 91 percent / aq. citric acid
2.1: Et3N / toluene / 5 h / 70 °C
3.1: 93 percent / aq. K2CO3
4.1: 93 percent / PhSO3H / 5 h / 120 °C
View Scheme
Multi-step reaction with 3 steps
1.1: magnesium chloride / toluene / 6 h
1.2: 20 h / 25 - 50 °C
2.1: methanesulfonyl chloride / toluene / 1 h / 0 - 10 °C / Inert atmosphere
2.2: 3.5 h / 0 - 70 °C
3.1: benzenesulfonic acid / 5.5 h / 120 °C
View Scheme
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

ethyl (3R,4R,5S)-4-N-acetyl(1,1-dimethylethyl)amino-5-N,N-diallylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate
651324-07-1

ethyl (3R,4R,5S)-4-N-acetyl(1,1-dimethylethyl)amino-5-N,N-diallylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: MgCl2 / toluene / 23 h / 50 °C
1.2: 91 percent / aq. citric acid
2.1: Et3N / toluene / 5 h / 70 °C
3.1: 93 percent / aq. K2CO3
4.1: 93 percent / PhSO3H / 5 h / 120 °C
5.1: 95 percent / NaOAc / 4 h / 116 °C
View Scheme
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

(3R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-cyano-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester
382148-62-1

(3R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-cyano-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / toluene / 20 °C
2: 87 percent / imidasole / dimethylformamide / 20 °C
View Scheme
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

(1R,3S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-cyano-5-(1-ethyl-propoxy)-cyclohexanecarboxylic acid ethyl ester
382148-63-2

(1R,3S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-cyano-5-(1-ethyl-propoxy)-cyclohexanecarboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 85 percent / toluene / 20 °C
2: 87 percent / imidasole / dimethylformamide / 20 °C
3: 91 percent / H2 / Pd/C / ethyl acetate / 2585.81 Torr
View Scheme
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

(1R,3R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(1-ethyl-propoxy)-5-thiocarbamoyl-cyclohexanecarboxylic acid ethyl ester
382148-59-6

(1R,3R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(1-ethyl-propoxy)-5-thiocarbamoyl-cyclohexanecarboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 85 percent / toluene / 20 °C
2: 87 percent / imidasole / dimethylformamide / 20 °C
3: 91 percent / H2 / Pd/C / ethyl acetate / 2585.81 Torr
4: 73 percent / (TMS)2S; NaOMe / N,N-dimethyl-acetamide / 20 °C
View Scheme
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

(1R,3R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(1-ethyl-propoxy)-5-thiocarbamoyl-cyclohexanecarboxylic acid ethyl ester
382148-64-3

(1R,3R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(1-ethyl-propoxy)-5-thiocarbamoyl-cyclohexanecarboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 85 percent / toluene / 20 °C
2: 87 percent / imidasole / dimethylformamide / 20 °C
3: 91 percent / H2 / Pd/C / ethyl acetate / 2585.81 Torr
4: 7 percent / (TMS)2S; NaOMe / N,N-dimethyl-acetamide / 20 °C
View Scheme
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

(1R,3R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(1-ethyl-propoxy)-5-(4-phenyl-thiazol-2-yl)-cyclohexanecarboxylic acid ethyl ester

(1R,3R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(1-ethyl-propoxy)-5-(4-phenyl-thiazol-2-yl)-cyclohexanecarboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 85 percent / toluene / 20 °C
2: 87 percent / imidasole / dimethylformamide / 20 °C
3: 91 percent / H2 / Pd/C / ethyl acetate / 2585.81 Torr
4: 73 percent / (TMS)2S; NaOMe / N,N-dimethyl-acetamide / 20 °C
5: 9 percent / dimethylformamide / 1 h / 20 °C
View Scheme
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

(1R,3R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(1-ethyl-propoxy)-5-(4-phenyl-thiazol-2-yl)-cyclohexanecarboxylic acid ethyl ester

(1R,3R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(1-ethyl-propoxy)-5-(4-phenyl-thiazol-2-yl)-cyclohexanecarboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 85 percent / toluene / 20 °C
2: 87 percent / imidasole / dimethylformamide / 20 °C
3: 91 percent / H2 / Pd/C / ethyl acetate / 2585.81 Torr
4: 73 percent / (TMS)2S; NaOMe / N,N-dimethyl-acetamide / 20 °C
5: 74 percent / dimethylformamide / 1 h / 20 °C
View Scheme

(1S,5R,6S)-Ethyl 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate Chemical Properties

Molecular structure of 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate (CAS NO.204254-96-6) is:

Product Name: 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate
CAS Registry Number: 204254-96-6
Systematic Name: ethyl 5-(1-ethylpropoxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylate
Empirical Formula: C14H22O4
Molecular Weight: 254.3221
Index of Refraction: 1.491
Molar Refractivity: 67.71 cm3
Molar Volume: 233.4 cm3
Surface Tension: 36.4 dyne/cm
Density: 1.08 g/cm3
Flash Point: 145.1 °C
Enthalpy of Vaporization: 57.97 kJ/mol
Boiling Point: 336.5 °C at 760 mmHg
Vapour Pressure: 0.000112 mmHg at 25°C

(1S,5R,6S)-Ethyl 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate Specification

 (1S,5R,6S)-Ethyl 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate , its cas register number is 204254-96-6. It also can be called [1S-(1a,5b,6a)]-5-(1-Ethylpropoxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester ; Ethyl(3r,4s,5s)-4,5-Epoxy-3-(1-Ethyl-Propoxy)-Cyclohex-1-Ene-1-Carboxylate .

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