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CAS No.: | 253265-97-3 |
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Name: | [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate |
Article Data: | 17 |
Molecular Structure: | |
Formula: | C11H13 N O7 |
Molecular Weight: | 271.227 |
Synonyms: | 2,5-Pyrrolidinedione,1-[[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl]oxy]carbonyl]oxy]- (9CI) |
EINECS: | 813-811-7 |
Density: | 1.51 g/cm3 |
Melting Point: | 122-125℃ |
Boiling Point: | 391.8 °C at 760 mmHg |
Flash Point: | 190.7 °C |
PSA: | 91.37000 |
LogP: | -0.09710 |
1-hydroxy-pyrrolidine-2,5-dione
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
Conditions | Yield |
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With triethylamine In tetrahydrofuran for 2h; Reflux; | 99.6% |
di(succinimido) carbonate
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
Conditions | Yield |
---|---|
With pyridine In tert-butyl methyl ether at 25 - 40℃; for 62h; Solvent; | 90% |
With triethylamine In acetonitrile at 23℃; for 7h; | 66% |
With triethylamine In dichloromethane Solvent; Reagent/catalyst; Inert atmosphere; Reflux; Large scale; | 62% |
γ-benzyloxymethyl-α,β-butenolide
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: benzophenone / 9 h / 0 °C / UV-irradiation 2: 89 percent / H2 / Pd/C / methanol / 24 h / 23 °C 3: LiAlH4 / tetrahydrofuran / 4 h / 0 °C 4: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3 5: triphenylphosphine; diisopropyl azodicarboxylate / benzene / 1.5 h / 23 °C 6: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C 7: 66 percent / Et3N / acetonitrile / 7 h / 23 °C View Scheme | |
Multi-step reaction with 7 steps 1: benzophenone / 9 h / 0 °C / UV-irradiation 2: 89 percent / H2 / Pd/C / methanol / 24 h / 23 °C 3: LiAlH4 / tetrahydrofuran / 4 h / 0 °C 4: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3 5: 94 percent / 4-methylmorpholino-N-oxide; tetrapropylammonium perruthenate / CH2Cl2 / 0.17 h / 23 °C 6: 70 percent / NaBH4 / ethanol / 2.5 h / -18 °C 7: 66 percent / Et3N / acetonitrile / 7 h / 23 °C View Scheme |
(5S)-5-(hydroxymethyl)-5H-furan-2-one
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: benzophenone / 4 h / 0 °C / UV-irradiation 2: LiAlH4 / tetrahydrofuran / 4 h / 0 °C 3: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3 4: triphenylphosphine; diisopropyl azodicarboxylate / benzene / 1.5 h / 23 °C 5: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C 6: 66 percent / Et3N / acetonitrile / 7 h / 23 °C View Scheme | |
Multi-step reaction with 6 steps 1: benzophenone / 4 h / 0 °C / UV-irradiation 2: LiAlH4 / tetrahydrofuran / 4 h / 0 °C 3: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3 4: 94 percent / 4-methylmorpholino-N-oxide; tetrapropylammonium perruthenate / CH2Cl2 / 0.17 h / 23 °C 5: 70 percent / NaBH4 / ethanol / 2.5 h / -18 °C 6: 66 percent / Et3N / acetonitrile / 7 h / 23 °C View Scheme |
methyl (2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 97 percent / H2SO4 / methanol / 2 h / 23 °C 2: benzophenone / 4 h / 0 °C / UV-irradiation 3: LiAlH4 / tetrahydrofuran / 4 h / 0 °C 4: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3 5: triphenylphosphine; diisopropyl azodicarboxylate / benzene / 1.5 h / 23 °C 6: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C 7: 66 percent / Et3N / acetonitrile / 7 h / 23 °C View Scheme | |
Multi-step reaction with 7 steps 1: 97 percent / H2SO4 / methanol / 2 h / 23 °C 2: benzophenone / 4 h / 0 °C / UV-irradiation 3: LiAlH4 / tetrahydrofuran / 4 h / 0 °C 4: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3 5: 94 percent / 4-methylmorpholino-N-oxide; tetrapropylammonium perruthenate / CH2Cl2 / 0.17 h / 23 °C 6: 70 percent / NaBH4 / ethanol / 2.5 h / -18 °C 7: 66 percent / Et3N / acetonitrile / 7 h / 23 °C View Scheme |
(4S,5S)-4-(1,3-dioxolan-2-yl)-5-hydroxymethyldihydrofuran-2-one
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: LiAlH4 / tetrahydrofuran / 4 h / 0 °C 2: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3 3: triphenylphosphine; diisopropyl azodicarboxylate / benzene / 1.5 h / 23 °C 4: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C 5: 66 percent / Et3N / acetonitrile / 7 h / 23 °C View Scheme | |
Multi-step reaction with 5 steps 1: LiAlH4 / tetrahydrofuran / 4 h / 0 °C 2: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3 3: 94 percent / 4-methylmorpholino-N-oxide; tetrapropylammonium perruthenate / CH2Cl2 / 0.17 h / 23 °C 4: 70 percent / NaBH4 / ethanol / 2.5 h / -18 °C 5: 66 percent / Et3N / acetonitrile / 7 h / 23 °C View Scheme |
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C 2: 66 percent / Et3N / acetonitrile / 7 h / 23 °C View Scheme |
(3aR,6aR)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-3(2H)-one
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 70 percent / NaBH4 / ethanol / 2.5 h / -18 °C 2: 66 percent / Et3N / acetonitrile / 7 h / 23 °C View Scheme |
(3S,3aS,6aR)-3-hydroxyhexahydrofuro[2,3-b]furan
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: triphenylphosphine; diisopropyl azodicarboxylate / benzene / 1.5 h / 23 °C 2: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C 3: 66 percent / Et3N / acetonitrile / 7 h / 23 °C View Scheme | |
Multi-step reaction with 3 steps 1: 94 percent / 4-methylmorpholino-N-oxide; tetrapropylammonium perruthenate / CH2Cl2 / 0.17 h / 23 °C 2: 70 percent / NaBH4 / ethanol / 2.5 h / -18 °C 3: 66 percent / Et3N / acetonitrile / 7 h / 23 °C View Scheme |
(S)-1-(benzyloxy)but-3-en-2-yl acrylate
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 98 percent / second generation Grubb's catalyst / CH2Cl2 / 5 h / Heating 2: benzophenone / 9 h / 0 °C / UV-irradiation 3: 89 percent / H2 / Pd/C / methanol / 24 h / 23 °C 4: LiAlH4 / tetrahydrofuran / 4 h / 0 °C 5: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3 6: triphenylphosphine; diisopropyl azodicarboxylate / benzene / 1.5 h / 23 °C 7: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C 8: 66 percent / Et3N / acetonitrile / 7 h / 23 °C View Scheme | |
Multi-step reaction with 8 steps 1: 98 percent / second generation Grubb's catalyst / CH2Cl2 / 5 h / Heating 2: benzophenone / 9 h / 0 °C / UV-irradiation 3: 89 percent / H2 / Pd/C / methanol / 24 h / 23 °C 4: LiAlH4 / tetrahydrofuran / 4 h / 0 °C 5: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3 6: 94 percent / 4-methylmorpholino-N-oxide; tetrapropylammonium perruthenate / CH2Cl2 / 0.17 h / 23 °C 7: 70 percent / NaBH4 / ethanol / 2.5 h / -18 °C 8: 66 percent / Et3N / acetonitrile / 7 h / 23 °C View Scheme |
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Molecule structure of [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate (CAS NO.253265-97-3):
Molecular Weight: 271.2234 g/mol
Molecular Formula: C11H13NO7
Density: 1.51 g/cm3
Boiling Point: 391.8 °C at 760 mmHg
Flash Point: 190.7 °C
Index of Refraction: 1.562
Molar Refractivity: 57.98 cm3
Molar Volume: 178.5 cm3
Polarizability: 22.98×10-24 cm3
Surface Tension: 61 dyne/cm
Enthalpy of Vaporization: 64.14 kJ/mol
Vapour Pressure: 2.41E-06 mmHg at 25 °C
InChI: InChI=1/C11H13NO7/c13-8-1-2-9(14)12(8)19-11(15)18-7-5-17-10-6(7)3-4-16-10/h6-7,10H,1-5H2/t6-,7-,10+/m0/s1
InChIKey: VCFNCYVHQSHFRH-MHYGZLNHBY
Product Categories: Chiral Reagents; Heterocycles; Intermediates
[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate (CAS NO.253265-97-3) is used as darunavir intermediate.
[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate (CAS NO.253265-97-3) is also named as 1-[[[[(3R,3aS,6aR)-Hexahydrofuro[2,3-β]furan-3-yl]oxy]carbonyl]oxy]-2,5-pyrrolidinedione ; Carbonic Acid 2,5-Dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-Hexahydrofuro[2,3-β]furan-3-yl] Ester ; [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-b]furanyl Succinimidyl Carbonate ; 1-[[[[(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl]oxy]carbonyl]oxy]-2,5-pyrrolidinedione;Carbonic Acid 2,5-Dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl] Ester . [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate (CAS NO.253265-97-3) is pale-yellow solid.