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

Name
[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate
EINECS 813-811-7
CAS No. 253265-97-3
Article Data17
CAS DataBase
Density 1.51 g/cm³
Solubility
Melting Point 122-125℃
Formula C11H13 N O7
Boiling Point 391.8 °C at 760 mmHg
Molecular Weight 271.227
Flash Point 190.7 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2,5-Pyrrolidinedione,1-[[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl]oxy]carbonyl]oxy]- (9CI)
PSA 91.37000
LogP -0.09710

Synthetic route

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

: C7H9ClO4

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions

Conditions	Yield
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

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%

: 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

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

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

: 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

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

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

: 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

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

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

: 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

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

: 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

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

: 809286-93-9
(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

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

: 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

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

: 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

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

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

: 681463-04-7
(2S,53)-3-(1,3-dioxolan-2-yl)pentane-1,2,5-triol

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3 2: triphenylphosphine; diisopropyl azodicarboxylate / benzene / 1.5 h / 23 °C 3: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C 4: 66 percent / Et3N / acetonitrile / 7 h / 23 °C View Scheme
Multi-step reaction with 4 steps 1: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3 2: 94 percent / 4-methylmorpholino-N-oxide; tetrapropylammonium perruthenate / CH2Cl2 / 0.17 h / 23 °C 3: 70 percent / NaBH4 / ethanol / 2.5 h / -18 °C 4: 66 percent / Et3N / acetonitrile / 7 h / 23 °C View Scheme

: 681463-03-6
(4S,5S)-5-(benzyloxymethyl)-4-(1,3-dioxolan-2-yl)dihydrofuran-2-one

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 89 percent / H2 / Pd/C / methanol / 24 h / 23 °C 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: 89 percent / H2 / Pd/C / methanol / 24 h / 23 °C 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

Yield

Multi-step reaction with 6 steps
1: 89 percent / H2 / Pd/C / methanol / 24 h / 23 °C
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: 89 percent / H2 / Pd/C / methanol / 24 h / 23 °C
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

: 108-05-4
vinyl acetate

: 74124-79-1
di(succinimido) carbonate

: 109789-19-7
(3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

A: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

B: (3S,3aS,6aR)-perhydrofuro[2,3-b]furan-3-yl acetate

Conditions

Conditions	Yield
Stage #1: vinyl acetate; (3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol In dichloromethane; tert-butyl methyl ether at 20℃; for 5h; Resolution of racemate; Large scale reaction; Enzymatic reaction; Stage #2: di(succinimido) carbonate With triethylamine In acetonitrile at 20℃; for 24h; enantioselective reaction;	A 5.1 g B n/a

...Expand

: 3,4-dihydroxy-2-(2-hydroxyethyl)butanal

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogenchloride / water / 20 h / 2 - 5 °C 1.2: 1 h 2.1: triethylamine / acetonitrile / 5 h / 20 °C / Inert atmosphere View Scheme

: 74124-79-1
di(succinimido) carbonate

: (3S,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

Conditions	Yield
With triethylamine In acetonitrile at 24 - 45℃; for 1h;

: (3SR,3aRS,6aSR)-3-hydroxy-4H-hexahydrofuro<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

Conditions	Yield
Multi-step reaction with 2 steps 1: Lipase PS / 24 h / 50 °C / Enzymatic reaction 2: triethylamine / acetonitrile / 24 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: lipase AS / 24 h / 50 °C / Enzymatic reaction 2: triethylamine / acetonitrile / 24 h / 20 °C / Inert atmosphere View Scheme

: 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

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 3 h / 50 °C 2: triethylamine / tetrahydrofuran / 2 h / Reflux View Scheme

: 109789-19-7
hexahydrofuro[2,3-b]furan-3-ol

: 74124-79-1
di(succinimido) carbonate

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions

Conditions	Yield
With pyridine In toluene at 40℃; for 9h;	71.9 g

: 36326-38-2, 64520-58-7, 91057-97-5, 91926-90-8, 104321-63-3, 124818-64-0, 128525-67-7, 128525-69-9, 104321-62-2
ethyl (E)-3-[(R)-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

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 25 h / 0 - 30 °C 2.1: sodium tetrahydroborate; lithium bromide / tetrahydrofuran / 35 h / 0 - 30 °C 2.2: 0.33 h / 25 - 30 °C / Inert atmosphere 2.3: 5 h / 0 - 30 °C / Inert atmosphere 3.1: pyridine / dichloromethane / 17 h / 40 - 45 °C View Scheme
Multi-step reaction with 4 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 25 h / 0 - 30 °C 2: lithium bromide; lithium borohydride / tetrahydrofuran / 18 h / 0 - 30 °C / Inert atmosphere 3: sulfuric acid; sodium hydroxide / water / 2 h / 5 - 30 °C 4: pyridine / dichloromethane / 17 h / 40 - 45 °C View Scheme
Multi-step reaction with 5 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 25 h / 0 - 30 °C 2.1: methanol; hydrogenchloride / 3 h / 25 - 30 °C 3.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 3 h / 65 - 70 °C 4.1: potassium tert-butylate / methanol / 0.17 h / 25 - 30 °C 4.2: 3 h / 0 - 30 °C 5.1: pyridine / dichloromethane / 17 h / 40 - 45 °C View Scheme

: ethyl 3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-nitrobutanoate

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate; lithium bromide / tetrahydrofuran / 35 h / 0 - 30 °C 1.2: 0.33 h / 25 - 30 °C / Inert atmosphere 1.3: 5 h / 0 - 30 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 17 h / 40 - 45 °C View Scheme
Multi-step reaction with 3 steps 1: lithium bromide; lithium borohydride / tetrahydrofuran / 18 h / 0 - 30 °C / Inert atmosphere 2: sulfuric acid; sodium hydroxide / water / 2 h / 5 - 30 °C 3: pyridine / dichloromethane / 17 h / 40 - 45 °C View Scheme
Multi-step reaction with 4 steps 1.1: methanol; hydrogenchloride / 3 h / 25 - 30 °C 2.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 3 h / 65 - 70 °C 3.1: potassium tert-butylate / methanol / 0.17 h / 25 - 30 °C 3.2: 3 h / 0 - 30 °C 4.1: pyridine / dichloromethane / 17 h / 40 - 45 °C View Scheme

: (S)-5-Hydroxymethyl-4-nitromethyl-dihydro-furan-2-one

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 3 h / 65 - 70 °C 2.1: potassium tert-butylate / methanol / 0.17 h / 25 - 30 °C 2.2: 3 h / 0 - 30 °C 3.1: pyridine / dichloromethane / 17 h / 40 - 45 °C View Scheme

: C6H13NO5

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium tert-butylate / methanol / 0.17 h / 25 - 30 °C 1.2: 3 h / 0 - 30 °C 2.1: pyridine / dichloromethane / 17 h / 40 - 45 °C View Scheme

: 3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-nitrobutan-1-ol

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; sodium hydroxide / water / 2 h / 5 - 30 °C 2: pyridine / dichloromethane / 17 h / 40 - 45 °C View Scheme

: 59256-86-9
ethyl 2-((3aR,5S,6R,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl)acetate

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1.1: sodium periodate / methanol / 2 h / 0 - 23 °C 2.1: sodium tetrahydroborate / methanol / 1 h / 0 °C 3.1: triethylamine / dichloromethane / 18 h / 0 - 23 °C / Inert atmosphere 4.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C 4.2: 6 h / -78 - 23 °C 5.1: potassium carbonate / methanol / 0.25 h / 0 °C 6.1: disodium hydrogenphosphate; Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C 7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C 8.1: hydrogenchloride / methanol / 12 h / 0 - 23 °C 9.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 - 23 °C / Inert atmosphere 9.2: 1.5 h / 0 °C 9.3: 1 h / 0 - 23 °C 10.1: triethylamine / acetonitrile / 16 h / 23 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 10 steps
1.1: sodium periodate / methanol / 2 h / 0 - 23 °C
2.1: sodium tetrahydroborate / methanol / 1 h / 0 °C
3.1: triethylamine / dichloromethane / 18 h / 0 - 23 °C / Inert atmosphere
4.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C
4.2: 6 h / -78 - 23 °C
5.1: potassium carbonate / methanol / 0.25 h / 0 °C
6.1: disodium hydrogenphosphate; Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C
7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C
8.1: hydrogenchloride / methanol / 12 h / 0 - 23 °C
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 - 23 °C / Inert atmosphere
9.2: 1.5 h / 0 °C
9.3: 1 h / 0 - 23 °C
10.1: triethylamine / acetonitrile / 16 h / 23 °C / Inert atmosphere
View Scheme

: 178557-39-6
ethyl 2-[(3aR,5S,6R,6aR)-5-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl]acetate

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: triethylamine / dichloromethane / 18 h / 0 - 23 °C / Inert atmosphere 2.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C 2.2: 6 h / -78 - 23 °C 3.1: potassium carbonate / methanol / 0.25 h / 0 °C 4.1: disodium hydrogenphosphate; Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C 5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C 6.1: hydrogenchloride / methanol / 12 h / 0 - 23 °C 7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 - 23 °C / Inert atmosphere 7.2: 1.5 h / 0 °C 7.3: 1 h / 0 - 23 °C 8.1: triethylamine / acetonitrile / 16 h / 23 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 8 steps
1.1: triethylamine / dichloromethane / 18 h / 0 - 23 °C / Inert atmosphere
2.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C
2.2: 6 h / -78 - 23 °C
3.1: potassium carbonate / methanol / 0.25 h / 0 °C
4.1: disodium hydrogenphosphate; Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C
5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C
6.1: hydrogenchloride / methanol / 12 h / 0 - 23 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 - 23 °C / Inert atmosphere
7.2: 1.5 h / 0 °C
7.3: 1 h / 0 - 23 °C
8.1: triethylamine / acetonitrile / 16 h / 23 °C / Inert atmosphere
View Scheme

: 58399-68-1
(3aS,4S,6aR)-2-Oxo-hexahydro-furo[3,4-b]furan-4-carbaldehyde

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C 2.1: hydrogenchloride / methanol / 12 h / 0 - 23 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 - 23 °C / Inert atmosphere 3.2: 1.5 h / 0 °C 3.3: 1 h / 0 - 23 °C 4.1: triethylamine / acetonitrile / 16 h / 23 °C / Inert atmosphere View Scheme

: 57466-98-5
(Z)-ethyl 2-((3aR,5S,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethylfuro[2,3-d][1,3]dioxol-6(3aH,5H,6aH)-ylidene)acetate

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: water; acetic acid / 60 h / 23 °C 2.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C 2.2: 6 h / -78 - 23 °C 3.1: potassium carbonate / methanol / 0.25 h / 0 °C 4.1: disodium hydrogenphosphate; Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C 5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C 6.1: hydrogenchloride / methanol / 12 h / 0 - 23 °C 7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 - 23 °C / Inert atmosphere 7.2: 1.5 h / 0 °C 7.3: 1 h / 0 - 23 °C 8.1: triethylamine / acetonitrile / 16 h / 23 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 8 steps
1.1: water; acetic acid / 60 h / 23 °C
2.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C
2.2: 6 h / -78 - 23 °C
3.1: potassium carbonate / methanol / 0.25 h / 0 °C
4.1: disodium hydrogenphosphate; Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C
5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C
6.1: hydrogenchloride / methanol / 12 h / 0 - 23 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 - 23 °C / Inert atmosphere
7.2: 1.5 h / 0 °C
7.3: 1 h / 0 - 23 °C
8.1: triethylamine / acetonitrile / 16 h / 23 °C / Inert atmosphere
View Scheme

: 950583-17-2
(Z)-ethyl 2-((3aR,5S,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ylidene)acetate

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1.1: palladium 10% on activated carbon; hydrogen / ethanol / 24 h / 760.05 Torr 2.1: sodium periodate / methanol / 2 h / 0 - 23 °C 3.1: sodium tetrahydroborate / methanol / 1 h / 0 °C 4.1: triethylamine / dichloromethane / 18 h / 0 - 23 °C / Inert atmosphere 5.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C 5.2: 6 h / -78 - 23 °C 6.1: potassium carbonate / methanol / 0.25 h / 0 °C 7.1: disodium hydrogenphosphate; Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C 8.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C 9.1: hydrogenchloride / methanol / 12 h / 0 - 23 °C 10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 - 23 °C / Inert atmosphere 10.2: 1.5 h / 0 °C 10.3: 1 h / 0 - 23 °C 11.1: triethylamine / acetonitrile / 16 h / 23 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 11 steps
1.1: palladium 10% on activated carbon; hydrogen / ethanol / 24 h / 760.05 Torr
2.1: sodium periodate / methanol / 2 h / 0 - 23 °C
3.1: sodium tetrahydroborate / methanol / 1 h / 0 °C
4.1: triethylamine / dichloromethane / 18 h / 0 - 23 °C / Inert atmosphere
5.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C
5.2: 6 h / -78 - 23 °C
6.1: potassium carbonate / methanol / 0.25 h / 0 °C
7.1: disodium hydrogenphosphate; Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C
8.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C
9.1: hydrogenchloride / methanol / 12 h / 0 - 23 °C
10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 - 23 °C / Inert atmosphere
10.2: 1.5 h / 0 °C
10.3: 1 h / 0 - 23 °C
11.1: triethylamine / acetonitrile / 16 h / 23 °C / Inert atmosphere
View Scheme

: 1008743-57-4
3-deoxy-3-(2-ethoxy-2-oxoethyl)-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: sodium tetrahydroborate / methanol / 1 h / 0 °C 2.1: triethylamine / dichloromethane / 18 h / 0 - 23 °C / Inert atmosphere 3.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C 3.2: 6 h / -78 - 23 °C 4.1: potassium carbonate / methanol / 0.25 h / 0 °C 5.1: disodium hydrogenphosphate; Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C 6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C 7.1: hydrogenchloride / methanol / 12 h / 0 - 23 °C 8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 - 23 °C / Inert atmosphere 8.2: 1.5 h / 0 °C 8.3: 1 h / 0 - 23 °C 9.1: triethylamine / acetonitrile / 16 h / 23 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 9 steps
1.1: sodium tetrahydroborate / methanol / 1 h / 0 °C
2.1: triethylamine / dichloromethane / 18 h / 0 - 23 °C / Inert atmosphere
3.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C
3.2: 6 h / -78 - 23 °C
4.1: potassium carbonate / methanol / 0.25 h / 0 °C
5.1: disodium hydrogenphosphate; Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C
6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C
7.1: hydrogenchloride / methanol / 12 h / 0 - 23 °C
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 - 23 °C / Inert atmosphere
8.2: 1.5 h / 0 °C
8.3: 1 h / 0 - 23 °C
9.1: triethylamine / acetonitrile / 16 h / 23 °C / Inert atmosphere
View Scheme

: ((3aR,5R,6aS)-2,2-dimethyl-6-oxotetrahydrofuro[2,3-d][1,3]-dioxol-5-yl)methyl benzoate

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: palladium 10% on activated carbon; hydrogen / ethanol / 6 h / 23 °C 2.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C 2.2: 6 h / -78 - 23 °C 3.1: potassium carbonate / methanol / 0.25 h / 0 °C 4.1: disodium hydrogenphosphate; Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C 5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C 6.1: hydrogenchloride / methanol / 12 h / 0 - 23 °C 7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 - 23 °C / Inert atmosphere 7.2: 1.5 h / 0 °C 7.3: 1 h / 0 - 23 °C 8.1: triethylamine / acetonitrile / 16 h / 23 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 8 steps
1.1: palladium 10% on activated carbon; hydrogen / ethanol / 6 h / 23 °C
2.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C
2.2: 6 h / -78 - 23 °C
3.1: potassium carbonate / methanol / 0.25 h / 0 °C
4.1: disodium hydrogenphosphate; Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C
5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C
6.1: hydrogenchloride / methanol / 12 h / 0 - 23 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 - 23 °C / Inert atmosphere
7.2: 1.5 h / 0 °C
7.3: 1 h / 0 - 23 °C
8.1: triethylamine / acetonitrile / 16 h / 23 °C / Inert atmosphere
View Scheme

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ((2S,4S,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl)carbamate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 20℃; for 24h;	100%

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: 251105-80-3
N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride

: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-{(1S,2R)-2-hydroxy-3-[(2-methylpropyl)-4-nitrophenylsulfonylamino]-1-phenylmethylpropyl}carbamate

Conditions

Conditions	Yield
In tetrahydrofuran at 30℃; for 6h;	98.9%
With triethylamine In dichloromethane at 20℃; for 24h; Inert atmosphere;	95%
With triethylamine In dichloromethane

: 1-benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl-amine

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: 865105-52-8
[(2R,3S)-3-[[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl]oxy]carbonyl]amino]-2-hydroxy-4-phenylbutyl](2-methylpropyl)carbamic acid phenylmethyl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 24h;	96.4%
With N-ethyl-N,N-diisopropylamine In dichloromethane
With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.5h; Inert atmosphere;	5.8 g

: 1-benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl-ammonium chloride

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: 865105-52-8
[(2R,3S)-3-[[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl]oxy]carbonyl]amino]-2-hydroxy-4-phenylbutyl](2-methylpropyl)carbamic acid phenylmethyl ester

Conditions

Conditions	Yield
Stage #1: 1-benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl-ammonium chloride; 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione With triethylamine In dichloromethane at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate In dichloromethane; water	96.4%

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: 169280-56-2
4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide

: darunavir

Conditions

Conditions	Yield
In dimethyl sulfoxide at 15 - 30℃; Solvent;	94%
With triethylamine In dichloromethane at 20℃;	90%
With potassium carbonate In Isopropyl acetate; water at 15 - 35℃; for 4h;	83.33%

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: 159006-03-8
tert-butyl (1S,2R)-1-benzyl-2-hydroxy-3-{isobutyl[(4-methoxyphenyl)sulfonyl]amino}propylcarbamate

: 206362-00-7
{(1S,2R)-1-Benzyl-2-hydroxy-3-[isobutyl-(4-methoxy-benzenesulfonyl)-amino]-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Conditions

Conditions	Yield
Stage #1: tert-butyl (1S,2R)-1-benzyl-2-hydroxy-3-{isobutyl[(4-methoxyphenyl)sulfonyl]amino}propylcarbamate With trifluoroacetic acid In dichloromethane at 23℃; for 0.666667h; Stage #2: 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione With triethylamine In dichloromethane at 23℃; for 3h;	90%

: N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)(2-methylbenzimidazol-5-yl)sulfonamide

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: [(1S,2R)-2-hydroxy-3-[[(2-methylbenzimidazol-5-yl)sulfonyl](2-methylpropyl)amino]-1-(phenylmethyl)propyl]carbamic acid [(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl] ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 17h;	89%

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: 183004-94-6
3-S-(N-tert-butyloxyformamido)-[2R-hydroxy-1-[(4-aminophenylsulfonyl)(2-methylpropyl)]amino]-4-phenylbutane

: darunavir

Conditions

Conditions	Yield
Stage #1: 3-S-(N-tert-butyloxyformamido)-[2R-hydroxy-1-[(4-aminophenylsulfonyl)(2-methylpropyl)]amino]-4-phenylbutane With trifluoroacetic acid In dichloromethane at 23℃; for 0.666667h; Stage #2: 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione With triethylamine In dichloromethane at 23℃; for 3h;	89%

: 160233-05-6
N-[(1S,2R)-3-[[(benzo-[1,3]-dioxole-5-sulfonyl)](isobutyl)amino]-1-benzyl-2-hydroxypropyl]carbamic acid tert-butyl ester

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: GRL-98065

Conditions

Conditions	Yield
Stage #1: N-[(1S,2R)-3-[[(benzo-[1,3]-dioxole-5-sulfonyl)](isobutyl)amino]-1-benzyl-2-hydroxypropyl]carbamic acid tert-butyl ester With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Stage #2: 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione With triethylamine In acetonitrile at 20℃; for 4h; Further stages.;	82%
Stage #1: N-[(1S,2R)-3-[[(benzo-[1,3]-dioxole-5-sulfonyl)](isobutyl)amino]-1-benzyl-2-hydroxypropyl]carbamic acid tert-butyl ester With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Stage #2: 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione With triethylamine In acetonitrile at 20℃; for 4h;	82%

: C31H47BN2O7S

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: C33H47BN2O9S

Conditions

Conditions	Yield
Stage #1: C31H47BN2O7S With hydrogenchloride In 1,4-dioxane for 4h; Stage #2: 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione With triethylamine In dichloromethane at 20℃; Inert atmosphere;	82%

: C30H45BN2O7S

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: C32H45BN2O9S

Conditions

Conditions	Yield
Stage #1: C30H45BN2O7S With hydrogenchloride In 1,4-dioxane at 22℃; under 760.051 Torr; for 4h; Inert atmosphere; Stage #2: 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione With triethylamine In dichloromethane at 22℃; under 760.051 Torr; for 16h; Inert atmosphere;	82%

: N-((2R,3S)-4-(adamantan-1-yl)-3-amino-2-hydroxybutyl)-N-benzyl-4-methoxybenzenesulfonamide

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl ((2S,3R)-1-(adamantan-1-yl)-4-((N-benzyl-4-methoxyphenyl)-sulfonamido)-3-hydroxybutan-2-yl)carbamate

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 48h;	80%

: 660410-38-8
2-Dimethylamino-benzothiazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: {(1S,2R)-1-Benzyl-3-[(2-dimethylamino-benzothiazole-6-sulfonyl)-isobutyl-amino]-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h;	78%

: 473739-14-9
2-(2-Pyrrolidin-1-yl-ethylamino)-benzothiazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: ((1S,2R)-1-Benzyl-2-hydroxy-3-{isobutyl-[2-(2-pyrrolidin-1-yl-ethylamino)-benzothiazole-6-sulfonyl]-amino}-propyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h;	76%

: N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-4-(1,3-dioxoisoindolin-2-yl)-N-isobutylbenzenesulfonamide

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (2S,3R)-4-(4-(1,3-dioxoisoindolin-2-yl)-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate

Conditions

Conditions	Yield
With triethylamine In water; ethyl acetate at 25 - 35℃;	73.19%

: 2-[Methyl-(2-pyrrolidin-1-yl-ethyl)-amino]-benzothiazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: [(1S,2R)-1-Benzyl-2-hydroxy-3-(isobutyl-{2-[methyl-(2-pyrrolidin-1-yl-ethyl)-amino]-benzothiazole-6-sulfonyl}-amino)-propyl]-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h;	73%

: 1311412-72-2
C35H38ClFN4O4

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: 1311410-46-4
C42H46ClFN4O8

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 1h;	73%

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: 622866-42-6
{(1S,2R)-[1-(4-formyl-benzyl)]-(2R)-2-hydroxy-3-[N-isobutyl-(N-4-methoxy-benzenesulfonyl)-amino]-propyl}-carbamic acid [3R,3aS,6aR]-hexahydrofuro[2,3-b]furan-3-yl ester

Conditions

Conditions	Yield
Stage #1: C27H38N2O7S With methanesulfonic acid In tetrahydrofuran at 40℃; Stage #2: 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione With 1-methyl-1H-imidazole In tetrahydrofuran at 50℃; Product distribution / selectivity;	70%

: 470704-95-1
2-(2-Dimethylamino-ethylamino)-benzooxazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: ((1S,2R)-1-Benzyl-3-{[2-(2-dimethylamino-ethylamino)-benzooxazole-6-sulfonyl]-isobutyl-amino}-2-hydroxy-propyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h;	67%

: 1007876-78-9
C32H41N3O7S2

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: C34H41N3O9S2

Conditions

Conditions	Yield
Stage #1: C32H41N3O7S2 With hydrogenchloride In 1,4-dioxane at 20℃; for 0.333333h; Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane Stage #3: 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione With N-ethyl-N,N-diisopropylamine	67%

: 2-(3-Dimethylamino-propylamino)-benzothiazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: ((1S,2R)-1-Benzyl-3-{[2-(3-dimethylamino-propylamino)-benzothiazole-6-sulfonyl]-isobutyl-amino}-2-hydroxy-propyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h;	66%

: 2-(2-Methylamino-ethylamino)-benzothiazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: ((1S,2R)-1-Benzyl-2-hydroxy-3-{isobutyl-[2-(2-methylamino-ethylamino)-benzothiazole-6-sulfonyl]-amino}-propyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h;	64%

: N-((2R,3S)-4-(adamantan-1-yl)-3-amino-2-hydroxybutyl)-N-isobutyl-4-aminobenzenesulfonamide

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ((2S,3R)-1-(adamantan-1-yl)-4-((4-amino-N-isobutylphenyl)-sulfonamido)-3-hydroxybutan-2-yl)carbamate

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 40h;	62%

: N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)[1-(2-methylpropyl)benzimidazol-6-yl]sulfonamide hydrochloride

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: [(1S,2R)-2-hydroxy-3-[(2-methylpropyl)[[1-(2-methylpropyl)benzimidazol-6-yl]sulfonyl]amino]-1-(phenylmethyl)propyl]carbamic acid [(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl] ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 4h;	60%

: 473739-12-7
2-(2-Dimethylamino-ethylamino)-benzothiazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: ((1S,2R)-1-Benzyl-3-{[2-(2-dimethylamino-ethylamino)-benzothiazole-6-sulfonyl]-isobutyl-amino}-2-hydroxy-propyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h;	59%

: 1217206-75-1
C24H33N3O2S

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: 1217206-85-3
C31H41N3O6S

Conditions

Conditions	Yield
With triethylamine In dichloromethane	59%

: N-((2R,3S)-4-(adamantan-1-yl)-3-amino-2-hydroxybutyl)-N-isobutyl-4-methoxybenzenesulfonamide

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ((2S,3R)-1-(adamantan-1-yl)-3-hydroxy-4-((N-isobutyl-4-methoxyphenyl)sulfonamido)-butan-2-yl)carbamate

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 48h;	59%

: N-((2R,3S)-4-(adamantan-1-yl)-3-amino-2-hydroxybutyl)-4-methoxy-N-phenylbenzenesulfonamide

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl ((2S,3R)-1-(adamantan-1-yl)-3-hydroxy-4-((4-methoxy-N-phenylphenyl)sulfonamido)butan-2-yl)carbamate

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 58h;	58%

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

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

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

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

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

Product Name

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

Synthetic route

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

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

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

Related Products

Hot Products