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253265-97-3

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Basic Information
CAS No.: 253265-97-3
Name: [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate
Article Data: 17
Molecular Structure:
Molecular Structure of 253265-97-3 ([(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate)
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
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1-hydroxy-pyrrolidine-2,5-dione

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253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 2h; Reflux;99.6%
74124-79-1

di(succinimido) carbonate

156928-09-5

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
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%
72605-53-9

γ-benzyloxymethyl-α,β-butenolide

253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
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
78508-96-0

(5S)-5-(hydroxymethyl)-5H-furan-2-one

253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
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
81703-94-8

methyl (2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate

253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
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
140156-47-4

(4S,5S)-4-(1,3-dioxolan-2-yl)-5-hydroxymethyldihydrofuran-2-one

253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
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
186488-54-0

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate

253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
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
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(3aR,6aR)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-3(2H)-one

253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
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
252873-50-0

(3S,3aS,6aR)-3-hydroxyhexahydrofuro[2,3-b]furan

253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
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
681463-02-5

(S)-1-(benzyloxy)but-3-en-2-yl acrylate

253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
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
Raw Materials
156928-09-5
81703-94-8
74124-79-1
78508-96-0
681463-02-5
Downstream Products
156928-09-5
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  • [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate

  • Casno:

    253265-97-3

    [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate

    Min.Order: 1 Kilogram

    FOB Price:  USD $ 2.0-2.0

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  • [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate

  • Casno:

    253265-97-3

    [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate

    Min.Order: 1 Gram

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  • Carbonic acid,2,5-dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl] ester

  • Casno:

    253265-97-3

    Carbonic acid,2,5-dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl] ester

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  • Carbonic acid,2,5-dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl] ester

  • Casno:

    253265-97-3

    Carbonic acid,2,5-dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl] ester

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  • (3R,3aS,6aR)-3-Hydroxyhexahydrofuro[2,3-b]furanyl Succinimidyl Carbonate

  • Casno:

    253265-97-3

    (3R,3aS,6aR)-3-Hydroxyhexahydrofuro[2,3-b]furanyl Succinimidyl Carbonate

    Min.Order: 500 Gram

    FOB Price:  USD $ 0.0-0.0

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Chemistry

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

Uses

 [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate (CAS NO.253265-97-3) is used as darunavir intermediate.

Specification

 [(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.

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