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inquiry(1S,4R)-cis-4-Acetoxy-2-cyclopenten-1-ol Application:(1S,4R)-cis-4-Acetoxy-2-cyclopenten-1-ol
cis-1,4-diacetoxy-2-cyclopentene
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
With Novosyme sp 435 lipase In various solvent(s) at 20℃; for 18h; pH=8; | 96% |
With Novozym 435 | 96% |
With lipase from candida antartica In aq. phosphate buffer at 20℃; for 24h; pH=8; Enzymatic reaction; enantioselective reaction; | 96% |
cis-1,4-diacetoxy-2-cyclopentene
A
(1S,4R)-4-hydroxy-2-cyclopentenyl acetate
B
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
With methanol; lipase B from Candida antarctica In tert-butyl methyl ether at 5℃; for 16h; Enzymatic reaction; enantioselective reaction; | A n/a B 95% |
With sodium hydroxide; Esterase(porcine liver)PLE In water at 32℃; for 8h; Product distribution; further enzymes; pH=7, phosphate buffer; | |
With N-(2-acetamido)-2-aminoethanesulfonic acid; ethanolamine; 2-amino-2-hydroxymethyl-1,3-propanediol at 37℃; for 8h; Product distribution; antibody of IgG class: 37E8, pH 8.0; Km, Kcat, Ki; var. enzymes and time; |
(-)-acetic acid cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enyl ester
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol; ethyl acetate | 91% |
cis-4-cyclopentene-1,3-diol
acetic anhydride
A
cis-1,4-diacetoxy-2-cyclopentene
B
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
Stage #1: cis-4-cyclopentene-1,3-diol With (4-(pyridin-4-yl)-4,5-dihydro-3H-dinaphtho[2,1-c:1′,2′-e]azepine-2,6-diyl)bis(bis(4-((tertbutyldimethylsilyl)oxy)phenyl)methanol); N-ethyl-N,N-diisopropylamine In tert-butyl methyl ether at -40℃; for 0.25h; Stage #2: acetic anhydride In tert-butyl methyl ether at -40℃; for 6h; Temperature; Time; enantioselective reaction; | A n/a B 89% |
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
With Candida antartica lipase B In aq. phosphate buffer for 3.5h; pH=7; Enzymatic reaction; | 85% |
(1R,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-cyclopentene-1-yl acetate
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride | 82% |
vinyl acetate
A
cis-1,4-diacetoxy-2-cyclopentene
B
(1S,4R)-4-hydroxy-2-cyclopentenyl acetate
C
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
lipase EC 3.1.1.3 L10 In water; acetone at 5 - 25℃; for 6.5h; Product distribution / selectivity; | A n/a B 76.4% C n/a |
lipase EC 3.1.1.3 QLC In water; acetone at 5 - 25℃; for 6.5h; Product distribution / selectivity; | A n/a B 76.4% C n/a |
lipase EC 3.1.1.3 QL In water; acetone at 5 - 25℃; for 6.5h; Product distribution / selectivity; | A n/a B 75.5% C n/a |
lipase EC 3.1.1.3 QLG In water; acetone at 5 - 25℃; for 6.5h; Product distribution / selectivity; | A n/a B 61.9% C n/a |
pancreatin lipase In water; acetone at 5 - 25℃; for 6.5h; Product distribution / selectivity; | A n/a B 16.5% C n/a |
meso-cis-1,4-diacetoxy-2-cyclopentene
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
With novozyme 435 In aq. phosphate buffer at 4℃; for 18h; pH=6; pH-value; Temperature; Time; Enzymatic reaction; | 76% |
With porcine liver esterase; phosphate buffer at 37℃; for 48h; pH=7.0; Hydrolysis; | 34% |
With sodium hydroxide; Lipase PS Amano In water pH=7; Product distribution / selectivity; phosphate buffer; Enzymatic reaction; | n/a |
With sodium hydroxide; Novo SP435 In water pH=7; Product distribution / selectivity; phosphate buffer; Enzymatic reaction; |
vinyl acetate
cis-4-cyclopentene-1,3-diol
A
cis-1,4-diacetoxy-2-cyclopentene
B
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 2.5h; Ambient temperature; Pancreatin as lipase; | A 32% B 65% |
With triethylamine In tetrahydrofuran for 2h; Ambient temperature; Candida sp. 382 as lipase; | A 40% B 53% |
vinyl acetate
cis-4-cyclopentene-1,3-diol
A
cis-1,4-diacetoxy-2-cyclopentene
B
(1S,4R)-4-hydroxy-2-cyclopentenyl acetate
C
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; for 23h; Enzymatic reaction; enantioselective reaction; | A 25% B 61% C n/a |
2,2,2-trichloroethyl acetate
cis-4-cyclopentene-1,3-diol
A
(1S,4R)-4-hydroxy-2-cyclopentenyl acetate
B
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
pancreatin/base; |
3,5-Diacetoxycyclopentene
A
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
B
(1R,4R)-(+)-4-Hydroxy-2-cyclopentenyl acetate
Conditions | Yield |
---|---|
With potassium hydroxide; pig pancreatic lipase at 37℃; for 8h; 0.1 M phosphate buffer (pH 7); Yield given. Yields of byproduct given; |
Acetic acid (1R,4S)-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enyl ester
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol for 2h; Ambient temperature; Yield given; |
(1S,4R)-(-)-4-(2'R*-tetrahydropyranyloxy)-2-cyclopentenyl acetate
A
(1S,4R)-4-hydroxy-2-cyclopentenyl acetate
B
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol for 2h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With porcine liver esterase Hydrolysis; |
acetic anhydride
A
(1S,4S)-4-hydroxy-2-cyclopentenyl acetate
B
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
(1R,4S)-4-(tert-butyldimethylsilyloxy)cyclopent-2-enol
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 99 percent / Et3N; DMAP 2: 82 percent / TBAF View Scheme |
(2-furyl)methyl alcohol
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 53 percent / KH2PO4, H3PO4 / H2O / 40 h / 99 °C / pH 4.1 2: 76 percent / PPTs / tetrahydrofuran / 18 h / Ambient temperature 3: LiAlH4, LiI / various solvent(s); toluene / 0.5 h / -20 - -13 °C 4: 50 percent / Et3N, pancreatin, vinyl acetate / various solvent(s) / 7 h / Ambient temperature 5: DMAP / pyridine / 16 h / Ambient temperature 6: p-TsOH / ethanol / 2 h / Ambient temperature View Scheme | |
Multi-step reaction with 5 steps 1: 53 percent / KH2PO4, H3PO4 / H2O / 40 h / 99 °C / pH 4.1 2: 76 percent / PPTs / tetrahydrofuran / 18 h / Ambient temperature 3: LiAlH4, LiI / various solvent(s); toluene / 0.5 h / -20 - -13 °C 4: 45 percent / Et3N, pancreatin, vinyl acetate / various solvent(s) / 7 h / Ambient temperature 5: p-TsOH / ethanol / 2 h / Ambient temperature View Scheme | |
Multi-step reaction with 4 steps 1: potassium dihydrogenphosphate; phosphoric acid / water / 22 h / 25 - 99 °C / pH 4.1 2: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 2 h / -70 - -60 °C 3: dmap; triethylamine / N,N-dimethyl-formamide / 16 h / 10 - 30 °C / Inert atmosphere 4: disodium hydrogenphosphate / water / 14 h / 25 - 30 °C / pH 7 / Enzymatic reaction View Scheme |
4-Hydroxycyclopent-2-enone
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 76 percent / PPTs / tetrahydrofuran / 18 h / Ambient temperature 2: LiAlH4, LiI / various solvent(s); toluene / 0.5 h / -20 - -13 °C 3: 50 percent / Et3N, pancreatin, vinyl acetate / various solvent(s) / 7 h / Ambient temperature 4: DMAP / pyridine / 16 h / Ambient temperature 5: p-TsOH / ethanol / 2 h / Ambient temperature View Scheme | |
Multi-step reaction with 4 steps 1: 76 percent / PPTs / tetrahydrofuran / 18 h / Ambient temperature 2: LiAlH4, LiI / various solvent(s); toluene / 0.5 h / -20 - -13 °C 3: 45 percent / Et3N, pancreatin, vinyl acetate / various solvent(s) / 7 h / Ambient temperature 4: p-TsOH / ethanol / 2 h / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 2 h / -70 - -60 °C 2: dmap; triethylamine / N,N-dimethyl-formamide / 16 h / 10 - 30 °C / Inert atmosphere 3: disodium hydrogenphosphate / water / 14 h / 25 - 30 °C / pH 7 / Enzymatic reaction View Scheme |
(1R,4S)-(-)-4-(2'R*-tetrahydropyranyloxy)-2-cyclopentenol
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: DMAP / pyridine / 16 h / Ambient temperature 2: p-TsOH / ethanol / 2 h / Ambient temperature View Scheme |
4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enone
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: LiAlH4, LiI / various solvent(s); toluene / 0.5 h / -20 - -13 °C 2: 50 percent / Et3N, pancreatin, vinyl acetate / various solvent(s) / 7 h / Ambient temperature 3: DMAP / pyridine / 16 h / Ambient temperature 4: p-TsOH / ethanol / 2 h / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1: LiAlH4, LiI / various solvent(s); toluene / 0.5 h / -20 - -13 °C 2: 45 percent / Et3N, pancreatin, vinyl acetate / various solvent(s) / 7 h / Ambient temperature 3: p-TsOH / ethanol / 2 h / Ambient temperature View Scheme |
(+/-)-cis-4-(2'R*-tetrahydropyranyloxy)-2-cyclopentenol
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 50 percent / Et3N, pancreatin, vinyl acetate / various solvent(s) / 7 h / Ambient temperature 2: DMAP / pyridine / 16 h / Ambient temperature 3: p-TsOH / ethanol / 2 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: 45 percent / Et3N, pancreatin, vinyl acetate / various solvent(s) / 7 h / Ambient temperature 2: p-TsOH / ethanol / 2 h / Ambient temperature View Scheme |
cis-4-cyclopentene-1,3-diol
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dmap; triethylamine / N,N-dimethyl-formamide / 16 h / 10 - 30 °C / Inert atmosphere 2: disodium hydrogenphosphate / water / 14 h / 25 - 30 °C / pH 7 / Enzymatic reaction View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 23 h / 20 °C / Enzymatic reaction 2: lipase from candida antartica / aq. phosphate buffer / 24 h / 20 °C / pH 8 / Enzymatic reaction View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 24 h / 20 °C / Enzymatic reaction 2: lipase from candida antartica / aq. phosphate buffer / 24 h / 20 °C / pH 8 / Enzymatic reaction View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine; lipase from candida antartica / tetrahydrofuran / 0.5 h / 20 °C / Enzymatic reaction 2: lipase from candida antartica / aq. phosphate buffer / 24 h / 20 °C / pH 8 / Enzymatic reaction View Scheme |
6-oxabicyclo[3.1.0]hex-2-ene
acetic acid
A
(1S,4R)-4-hydroxy-2-cyclopentenyl acetate
B
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); Triethylene glycol dimethyl ether In tetrahydrofuran at 0℃; for 1h; Reagent/catalyst; Solvent; Schlenk technique; Inert atmosphere; Overall yield = 85 %Chromat.; | A n/a B n/a |
cyclopenta-1,3-diene
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III); 4-Phenylpyridine 1-oxide; sodium hypochlorite / dichloromethane / 5 h / 4 °C 2: Triethylene glycol dimethyl ether; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 1 h / 0 °C / Schlenk technique; Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: oxygen; thiourea; Rose Bengal lactone / methanol / 19 °C / 6000.6 Torr / Irradiation 2: dmap; pyridine / 2 h / 0 - 7 °C / Inert atmosphere 3: novozyme 435 / aq. phosphate buffer / 18 h / 4 °C / pH 6 / Enzymatic reaction View Scheme |
cis-1,4-diacetoxy-2-cyclopentene
A
cis-4-cyclopentene-1,3-diol
B
(1S,4R)-4-hydroxy-2-cyclopentenyl acetate
C
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
With pseudomonas fluorescens lipase In hexane; water at 25℃; Reagent/catalyst; Enzymatic reaction; enantioselective reaction; | |
With lipase B from Candida antarctica In aq. phosphate buffer at 20℃; pH=7.5; Solvent; Enzymatic reaction; | A n/a B n/a C n/a |
A
(1S,4R)-4-hydroxy-2-cyclopentenyl acetate
B
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
With recombinant pig liver esterase In aq. phosphate buffer at 50℃; for 2h; pH=7.5; pH-value; Temperature; Solvent; Enzymatic reaction; enantioselective reaction; | A n/a B n/a |
cis-3-acetoxy-5-hydroxycyclopent-1-ene
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1H-imidazole / dichloromethane / 0.17 h / 0 - 23 °C 2: Novozym 435 lipase / dichloromethane; aq. phosphate buffer / 23 - 24 °C / pH 8.0 View Scheme |
6-oxabicyclo[3.1.0]hex-2-ene
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.33 h / 0 °C 2: 1H-imidazole / dichloromethane / 0.17 h / 0 - 23 °C 3: Novozym 435 lipase / dichloromethane; aq. phosphate buffer / 23 - 24 °C / pH 8.0 View Scheme |
3,4-dihydro-2H-pyran
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Acetic acid (1R,4S)-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enyl ester
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid for 0.166667h; Ambient temperature; | 100% |
With pyridinium p-toluenesulfonate In dichloromethane | 96% |
With TSA In dichloromethane at 0℃; for 0.166667h; | 91% |
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
diethyl chlorophosphate
(1S,4R)-4-acetoxy-2-cyclopenten-1-yl diethyl phosphate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 25℃; for 4.5h; | 100% |
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
tert-butyldimethylsilyl chloride
(1R,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
With 1H-imidazole In tetrahydrofuran at 20℃; | 100% |
With 1H-imidazole In tetrahydrofuran at 20℃; for 24h; | 100% |
With 1H-imidazole In tetrahydrofuran at 20℃; for 24h; | 100% |
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
pivaloyl chloride
(3R,5S)-(+)-3-acetoxy-5-(trimethylacetyloxy)cyclopent-1-ene
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0℃; for 2h; | 100% |
With dmap; triethylamine In dichloromethane at 0℃; | 99% |
With dmap; triethylamine In dichloromethane at 0℃; for 0.75h; | 98% |
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
methanesulfonyl chloride
Acetic acid (1R,4R)-4-methanesulfonyloxy-cyclopent-2-enyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane Ambient temperature; | 100% |
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
1H-benzotriazole-1-carboxylic acid methyl ester 3-oxide
Conditions | Yield |
---|---|
With dmap; triethylamine In pyridine at 25℃; | 99% |
N-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)-N-[2-{[(2S,3R,6S)-2-methoxy-6-{(2-nitrophenylsulfonamido)methyl}-3,6-dihydro-2H-pyran-3-yloxy]methyl}allyl]-4-methylbenzenesulfonamide
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
C41H40F17N3O11S2
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; Fukuyama-Mitsunobu reaction; | 98% |
N-allyl-p-nitrobenzenesulfonamide
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
C16H18N2O6S
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 18h; Fukuyama Coupling; | 98% |
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
methyl chloroformate
methyl (1S,4R)-4-acetoxy-2-cyclopentenylcarbonate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 23℃; | 97% |
With pyridine In dichloromethane at 0℃; for 2h; | 97% |
With pyridine In dichloromethane at 0℃; for 1h; |
Allylchlorodimethylsilane
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 25℃; for 3h; Substitution; | 97% |
<2-(13)C>acetyl chloride
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 20℃; | 97% |
diiodomethane
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
(1S,2R,4S,5R)-(+)-4-hydroxybicyclo<3.1.0>hex-2-yl acetate
Conditions | Yield |
---|---|
Stage #1: (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate With Et2Zn In dichloromethane at 0℃; for 0.25h; Simmons-Smith cyclopropanation; Stage #2: diiodomethane With Et2Zn In hexane; dichloromethane at 0 - 20℃; | 97% |
Stage #1: (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate With diethylzinc In hexane; dichloromethane at 0℃; Stage #2: diiodomethane With diethylzinc In hexane; dichloromethane at 0 - 20℃; |
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; Fukuyama Coupling; Inert atmosphere; | 97% |
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
chloroformic acid ethyl ester
(1S,4R)-cis-1-ethoxycarbonyloxy-4-acetoxy-2-cyclopentene
Conditions | Yield |
---|---|
With pyridine at 0℃; for 1h; | 96.6% |
With pyridine In dichloromethane for 2h; Ambient temperature; | 92% |
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
(R)-4-acetoxycyclopent-2-en-1-one
Conditions | Yield |
---|---|
With dipyridinium dichromate | 96% |
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane | 94% |
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78℃; Swern oxidation; | 94% |
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
acetic anhydride
Conditions | Yield |
---|---|
With dmap In dichloromethane at 0℃; for 4h; | 95% |
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
chloromethyl methyl ether
Acetic acid (1R,4S)-4-methoxymethoxy-cyclopent-2-enyl ester
Conditions | Yield |
---|---|
With dmap; N-ethyl-N,N-diisopropylamine | 95% |
78% |
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
2,2,2-Trichloro-acetimidic acid (2R,3R,4S,5S,6R)-6-methyl-3,4,5-tris-triethylsilanyloxy-tetrahydro-pyran-2-yl ester
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In diethyl ether at -30℃; Etherification; | 95% |
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
methanesulfonyl chloride
Conditions | Yield |
---|---|
With triethylamine In dichloromethane | 95% |
With triethylamine In dichloromethane | 95% |
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
1(R)-acetoxy-2,3(R,R),4(S)-trihydroxycyclopentane
Conditions | Yield |
---|---|
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; acetone | 94% |
-butyl vinyl ether
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Acetic acid (1R,4S)-4-(1-butoxy-2-iodo-ethoxy)-cyclopent-2-enyl ester
Conditions | Yield |
---|---|
With N-iodo-succinimide In dichloromethane at 20℃; for 20h; | 93% |
Benzyloxymethyl chloride
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
(1S)-cis-4-Benzyloxymethylcyclopent-2-en-1-ol
Conditions | Yield |
---|---|
Stage #1: Benzyloxymethyl chloride With bromine; magnesium; mercury dichloride In tetrahydrofuran at -5℃; for 2.5h; Stage #2: (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate In tetrahydrofuran at -20℃; for 0.25h; Further stages.; | 92% |
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
di-tert-butyl [(1R,4S)-4-hydroxycyclopent-2-en-1-yl]imidodicarbonate
Conditions | Yield |
---|---|
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran | 92% |
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
ethyl vinyl ether
Conditions | Yield |
---|---|
With N-iodo-succinimide In dichloromethane at -20℃; for 4h; | 90% |
With N-iodo-succinimide |
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
malonic acid dimethyl ester
2-<(1R,4S)-4-hydroxycyclopent-2-enyl>malonsaeure-dimethylester
Conditions | Yield |
---|---|
With potassium tert-butylate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 2h; | 90% |
With potassium tert-butylate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 2h; Product distribution; Further Variations:; Reagents; Temperatures; reaction times; | 90% |
With potassium carbonate; triphenylphosphine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 40℃; for 12h; | 73% |
With tetrakis(triphenylphosphine) palladium(0); sodium hydride; triphenylphosphine 1.) THF, 2.) 1 h; Yield given. Multistep reaction; | |
With potassium tert-butylate; palladium |
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
4-nitro-benzoic acid
p-Nitrobenzoic acid (1R,4R)-4-acetoxycyclopent-2-en-1-yl ester
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Esterification; Mitsunobu reaction; | 90% |
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
chloroacetic acid
(1R,4R)-4-acetoxycyclopent-2-en-1-yl chloroacetate
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 2h; | 90% |
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