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

Name
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
EINECS 605-076-4
CAS No. 156928-09-5
Article Data50
CAS DataBase
Density 1.276 g/cm³
Solubility
Melting Point
Formula C₆H₁₀O₃
Boiling Point 251.463 °C at 760 mmHg
Molecular Weight 130.144
Flash Point 105.881 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Furo[2,3-b]furan-3-ol,hexahydro-, [3R-(3a,3ab,6ab)]-;3R,3AS,6aR-hexahydrofuro[2,3-b]furan-3-ol;R,S,R-Bisfuran alcohol;
PSA 38.69000
LogP -0.25990

Synthetic route

: 162119-35-9
3-acetoxy-(3R,3αS,6αR)-bis-tetrahydrofuran

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
With methanol; potassium carbonate at 20℃; Product distribution / selectivity;	100%
With potassium carbonate In methanol at 20℃;	30%
With methyllithium In tetrahydrofuran

: (2R,3S)-3-dimethoxymethyl-5-benzyloxy-1,2-pentanediol

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
Stage #1: (2R,3S)-3-dimethoxymethyl-5-benzyloxy-1,2-pentanediol With sulfuric acid In toluene at 0 - 35℃; for 15.5h; Stage #2: With palladium 10% on activated carbon; hydrogen at 25℃; for 6h; Stage #3: at 72 - 197℃; for 4.5h;	99%

: 809286-93-9
(3aR,6aR)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-3(2H)-one

A: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

B: 252873-50-0
(3S,3aS,6aR)-3-hydroxyhexahydrofuro[2,3-b]furan

Conditions

Conditions	Yield
Stage #1: (3aR,6aR)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-3(2H)-one With sodium tetrahydroborate In methanol; isopropyl alcohol at 0℃; for 1.5h; Stage #2: With ammonium chloride In methanol; isopropyl alcohol Product distribution / selectivity;	A 97.2% B n/a
Stage #1: (3aR,6aR)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-3(2H)-one With sodium tetrahydroborate In ethanol at -15℃; for 2h; Stage #2: With hydrogenchloride In ethanol; water Product distribution / selectivity;

: 725264-69-7
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl benzoate

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
With methanol; water; sodium hydroxide In tetrahydrofuran at 20℃; for 0.5h;	95%
With sodium hydroxide In water at 27 - 30℃; for 4h;	93%

: C6H10O4

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
With hydrogenchloride; diisobutylaluminium hydride In water; toluene at -50 - 60℃; for 16h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;	95%
With diisobutylaluminium hydride In toluene at -50 - 40℃; Inert atmosphere;	56.4 g

: C16H22O4

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol under 760.051 Torr; for 1h; Solvent;	91%

: C9H18O5

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
With hydrogenchloride In water at -2 - 5℃; Temperature;	90.4%

: (3SR,3aRS,6aSR)-3-hydroxy-4H-hexahydrofuro<2,3-b>furan

A: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

B: 162119-35-9
3-acetoxy-(3R,3αS,6αR)-bis-tetrahydrofuran

C: 162020-29-3
Acetic acid (3S,3aR,6aS)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Conditions

Conditions	Yield
With acetic anhydride In tert-butyl methyl ether at 20℃; for 110h; Reagent/catalyst; Enzymatic reaction;	A 90% B n/a C n/a
With acetic anhydride In 1,2-dimethoxyethane at 23℃; for 3h; Yield given. Yields of byproduct given;

...Expand

: exo-2,7-dioxabicyclo[3.2.0]hept-3-en-6-ylmethyl benzyl carbonate

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; tert-butyl methyl ether at 20℃; for 24h; Reagent/catalyst;	90%
With lipase Enzymatic reaction;

: (3SR,3aRS,6aSR)-3-hydroxy-4H-hexahydrofuro<2,3-b>furan

A: 156928-10-8
(3S,3aR,6aS)-3-hydroxyhexahydrofuro<2,3-b>furan

B: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

C: 162119-35-9
3-acetoxy-(3R,3αS,6αR)-bis-tetrahydrofuran

D: 162020-29-3
Acetic acid (3S,3aR,6aS)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Conditions

Conditions	Yield
With acetic anhydride In tert-butyl methyl ether at 20℃; for 110h; Reagent/catalyst; Enzymatic reaction;	A n/a B 90% C n/a D n/a

...Expand

: (3SR,3aRS,6aSR)-3-hydroxy-4H-hexahydrofuro<2,3-b>furan

A: 156928-10-8
(3S,3aR,6aS)-3-hydroxyhexahydrofuro<2,3-b>furan

B: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
With acetic anhydride In tert-butyl methyl ether at 20℃; for 110h; Reagent/catalyst; Enzymatic reaction;	A 90% B n/a

: 108-05-4
vinyl acetate

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

A: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

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

Conditions

Conditions	Yield
With Chirazyme L-2 In tert-butyl methyl ether at 25℃; for 40h; Enzymatic reaction;	A 90% B n/a

...Expand

: 362634-60-4
((R)-1-Naphthalen-1-yl-ethyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃;	86%

: 186488-54-0
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
With sodium methylate In methanol Mitsunobu Displacement; Inert atmosphere; stereoselective reaction;	82%
With lithium hydroxide; triethylamine In methanol; water at 23℃; for 2h;	326 mg

: 252873-50-0
(3S,3aS,6aR)-3-hydroxyhexahydrofuro[2,3-b]furan

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
Stage #1: (3S,3aS,6aR)-3-hydroxyhexahydrofuro[2,3-b]furan With di-isopropyl azodicarboxylate; triphenylphosphine; 4-nitro-benzoic acid In benzene at 23℃; for 1.5h; Mitsunobu reaction; Stage #2: With lithium hydroxide; triethylamine In methanol; water at 20℃; for 2h;	82%
Multi-step reaction with 2 steps 1: triphenylphosphine; diisopropyl azodicarboxylate / benzene / 1.5 h / 23 °C 2: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C View Scheme
Multi-step reaction with 2 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 View Scheme

: 809286-93-9
(3aR,6aR)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-3(2H)-one

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
With sodium tetrahydroborate In ethanol at -15 - 20℃; for 3h;	81%
With sodium tetrahydroborate; ethanol at 0℃; for 0.5h;	80%
With sodium tetrahydroborate In ethanol at -18℃; for 2.5h;	70%
With sodium tetrahydroborate In ethanol at -18℃; for 2.5h;	70%

: 115482-97-8
(2R,3R)-1,2-O-isopropylidene-3-vinyl-1,2,5-pentanetriol

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
Stage #1: (2R,3R)-1,2-O-isopropylidene-3-vinyl-1,2,5-pentanetriol With ozone Stage #2: With toluene-4-sulfonic acid	80%
Stage #1: (2R,3R)-1,2-O-isopropylidene-3-vinyl-1,2,5-pentanetriol With dimethylsulfide; ozone In methanol; dichloromethane at -78 - 20℃; for 3h; Inert atmosphere; Stage #2: toluene-4-sulfonic acid In methanol; chloroform for 1h; Reflux;	80%

: C11H20O5

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran at 50℃; for 6h; Solvent;	77%

: 866594-60-7
(3aS,4S,6aR)-4-methoxy-tetrahydro-furo[3.4-b]furan-2(3H)-one

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
Stage #1: (3aS,4S,6aR)-4-methoxy-tetrahydro-furo[3.4-b]furan-2(3H)-one With lithium borohydride In tetrahydrofuran at 50℃; for 2.5h; Stage #2: With hydrogenchloride In tetrahydrofuran at -10℃; for 2h;	76%

: ethyl (2R,3S)-3-(methyl(phenyl)carbamoyl)-5-oxotetrahydrofuran-2-carboxylate

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
Stage #1: ethyl (2R,3S)-3-(methyl(phenyl)carbamoyl)-5-oxotetrahydrofuran-2-carboxylate With lithium aluminium tetrahydride In tetrahydrofuran Stage #2: With sulfuric acid In dichloromethane; water; ethyl acetate; toluene at -10 - 80℃; for 68.15h;	75%
Stage #1: ethyl (2R,3S)-3-(methyl(phenyl)carbamoyl)-5-oxotetrahydrofuran-2-carboxylate With lithium aluminium tetrahydride In tetrahydrofuran at -10 - 20℃; for 17.25h; Stage #2: With sulfuric acid In tetrahydrofuran at -8 - 5℃; for 2h;	n/a

: C13H16O5

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
With sodium hydroxide In methanol at -15 - -5℃;	73.77%
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / 22 - 26 °C 2: sodium carbonate; methanol / 22 - 26 °C 3: hydrogenchloride / water / -2 - 5 °C View Scheme

: C14H24O5

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 60℃; for 6h; Solvent; Temperature;	72%

: (3aS,6aR)-4-methoxytetrahydrofuro[3,4-b]furan-2(3H)-one

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
Stage #1: (3aS,6aR)-4-methoxytetrahydrofuro[3,4-b]furan-2(3H)-one With lithium aluminium tetrahydride In tetrahydrofuran at -78 - 23℃; for 1h; Inert atmosphere; Stage #2: With sodium hydroxide In tetrahydrofuran; water at 0℃; for 1.5h; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 0 - 23℃; for 1h;	63%
Stage #1: (3aS,6aR)-4-methoxytetrahydrofuro[3,4-b]furan-2(3H)-one With sodium tetrahydroborate; lithium chloride In tetrahydrofuran at 25℃; Inert atmosphere; Reflux; Large scale; Stage #2: With hydrogenchloride In water at 10℃; for 2h; pH=1 - 3; Reagent/catalyst; Solvent; Inert atmosphere; Large scale;	80 kg

: 676999-02-3
(3S,4'R)-3-(2',2'-dimethyl-[1',3']dioxolane-4'-yl)tetrahydrofuran-2-ol

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
Stage #1: (3S,4'R)-3-(2',2'-dimethyl-[1',3']dioxolane-4'-yl)tetrahydrofuran-2-ol With hydrogenchloride In tetrahydrofuran; water at 20℃; for 23h; Stage #2: With potassium carbonate In tetrahydrofuran; water for 0.333333h;	61%
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 16h;
With hydrogenchloride; sodium bicarbonate; sodium chloride In tetrahydrofuran; water

: ethyl (2R,3S)-3-(ethyl(phenyl)carbamoyl)-5-oxotetrahydrofuran-2-carboxylate

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
Stage #1: ethyl (2R,3S)-3-(ethyl(phenyl)carbamoyl)-5-oxotetrahydrofuran-2-carboxylate With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 16h; Stage #2: With sulfuric acid In tetrahydrofuran at 20℃; for 3h;	54%

: 108-05-4
vinyl acetate

: (3SR,3aRS,6aSR)-3-hydroxy-4H-hexahydrofuro<2,3-b>furan

A: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

B: 162020-29-3
Acetic acid (3S,3aR,6aS)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Conditions

Conditions	Yield
With Lipase PS at 50℃; for 24h; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;	A 37% B 53%

...Expand

: 108-05-4
vinyl acetate

: (3SR,3aRS,6aSR)-3-hydroxy-4H-hexahydrofuro<2,3-b>furan

A: 156928-10-8
(3S,3aR,6aS)-3-hydroxyhexahydrofuro<2,3-b>furan

B: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

C: 162020-29-3
Acetic acid (3S,3aR,6aS)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Conditions

Conditions	Yield
With lipase AS at 50℃; for 24h; Enzymatic reaction; enantioselective reaction;	A n/a B 30% C 51%

...Expand

: C13H14O5

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
With diisobutylaluminium hydride In tetrahydrofuran at -74℃; for 1h; Temperature; Solvent; Inert atmosphere;	50%

: 1233923-19-7
ethyl (2R,3S)-3-(methoxy(methyl)carbamoyl)-5-oxotetrahydrofuran-2-carboxylate

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

Conditions

Conditions	Yield
Stage #1: ethyl (2R,3S)-3-(methoxy(methyl)carbamoyl)-5-oxotetrahydrofuran-2-carboxylate With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 16h; Stage #2: With sulfuric acid In tetrahydrofuran at 20℃; for 3h;	50%

: 108-24-7
acetic anhydride

: (3SR,3aRS,6aSR)-3-hydroxy-4H-hexahydrofuro<2,3-b>furan

A: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

B: 162020-29-3
Acetic acid (3S,3aR,6aS)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Conditions

Conditions	Yield
In 1,2-dimethoxyethane at 23℃; immobilized Amano lipase;	A n/a B 45%
Amano lipase 30 immobilized on Celite 521 In 1,2-dimethoxyethane at 23℃; Resolution of racemate;	A 42% B 45%
Amano lipase PS-C I In 1,2-dimethoxyethane Purification / work up; Resolution of racemate;	A 32% B n/a
With porcine pancreatic lipase (PPL) In tert-butyl methyl ether at 20℃; for 110h; Reagent/catalyst; Enzymatic reaction;

...Expand

: 98-88-4
benzoyl chloride

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

: 725264-69-7
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl benzoate

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 7h; enantioselective reaction;	97%

: 7693-46-1
4-Nitrophenyl chloroformate

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

: 192725-55-6
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-(4-nitrophenyl)carbonic acid

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0 - 23℃; for 12h; Inert atmosphere;	92%
With pyridine In dichloromethane	89%
With pyridine In ethyl acetate at 0℃; for 1h;	51.8%

: 24939-24-0
4-aminobenzenesulfonyl chloride

: 78-81-9
isobutylamine

: 530-62-1
1,1'-carbonyldiimidazole

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

: (S)-3-amino-(S)-2-hydroxy-4-phenyl-1-chlorobutane hydrochloride

: darunavir

Conditions

Conditions	Yield
Stage #1: 1,1'-carbonyldiimidazole; (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol In tetrahydrofuran for 1h; Stage #2: (S)-3-amino-(S)-2-hydroxy-4-phenyl-1-chlorobutane hydrochloride In tetrahydrofuran at 55 - 60℃; Stage #3: 4-aminobenzenesulfonyl chloride; isobutylamine	92%

...Expand

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

: 62-23-7
4-nitro-benzoic acid

: 186488-54-0
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate

Conditions

Conditions	Yield
With pyridine; triethylamine at 0 - 20℃;	92%

: 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%

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

: 1359057-78-5
C6H9IO2

Conditions

Conditions	Yield
With iodine; triphenylphosphine	90%

: 124-63-0
methanesulfonyl chloride

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

: C7H12O5S

Conditions

Conditions	Yield
With pyridine; triethylamine at 0 - 20℃; Reagent/catalyst;	90%

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

: 362634-64-8
(3S,3aR,6aR)-3-Iodo-hexahydro-furo[2,3-b]furan

Conditions

Conditions	Yield
With 1H-imidazole; iodine; triphenylphosphine In benzene at 60℃;	87%

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

: 809286-93-9
(3aR,6aR)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-3(2H)-one

Conditions

Conditions	Yield
With disodium hydrogenphosphate; Dess-Martin periodane In dichloromethane at 0 - 23℃; Dess-Martin oxidation; Inert atmosphere;	87%
With disodium hydrogenphosphate; Dess-Martin periodane In dichloromethane at 0 - 23℃; for 3h; Inert atmosphere;	87%
With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide In dichloromethane at 23℃; for 1h; Molecular sieve;
With disodium hydrogenphosphate; Dess-Martin periodane In dichloromethane at 0 - 23℃; Inert atmosphere;

: 7693-46-1
4-Nitrophenyl chloroformate

: 156928-10-8
(3S,3aR,6aS)-3-hydroxyhexahydrofuro<2,3-b>furan

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

: 854745-99-6
(3R,3aS,6aR) and (3S,3aR,6aS)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate

Conditions

Conditions	Yield
With 4-methyl-morpholine In dichloromethane at 0℃; for 16h;	86%

...Expand

: 524-38-9
N-hydroxyphthalimide

: 32315-10-9
bis(trichloromethyl) carbonate

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

: 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
Stage #1: bis(trichloromethyl) carbonate; (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol With pyridine In dichloromethane at 55℃; for 3h; Stage #2: N-hydroxyphthalimide In dichloromethane at 50℃; for 4h; Stage #3: N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride In toluene at 50℃; for 6h;	85.8%

...Expand

: 358-23-6
trifluoromethylsulfonic anhydride

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

: C7H9F3O5S

Conditions

Conditions	Yield
With dmap In dichloromethane at 0 - 20℃;	85%

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

: 32315-10-9
bis(trichloromethyl) carbonate

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

: 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
Stage #1: bis(trichloromethyl) carbonate; (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol With triethylamine In toluene at 90℃; for 3h; Stage #2: 1-hydroxy-pyrrolidine-2,5-dione In ethyl acetate at 50℃; for 3h; Stage #3: N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride In toluene at 50℃; for 6h;	84.9%

...Expand

: 74124-79-1
di(succinimido) carbonate

: 156928-09-5
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

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

: darunavir

Conditions

Conditions	Yield
With pyridine; triethylamine; methylamine In ethanol; water; acetonitrile Product distribution / selectivity;	81%
With triethylamine; methylamine In ethanol; water; ethyl acetate; acetonitrile	71%
Stage #1: di(succinimido) carbonate; (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol With pyridine In acetonitrile at 25 - 30℃; for 1h; Stage #2: 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide In acetonitrile at 0 - 5℃; for 0.5h; Stage #3: With triethylamine; methylamine In acetonitrile at 0 - 30℃;

...Expand

(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol Chemical Properties

Empirical Formula of (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol (CAS NO.156928-09-5): C₆H₁₀O₃
Molecular Weight: 130.1418
Index of Refraction: 1.51
Molar Refractivity: 30.524 cm³
Molar Volume: 102.025 cm³
Surface Tension: 45.459 dyne/cm
Density: 1.276 g/cm³
Flash Point: 105.881 °C
Enthalpy of Vaporization: 56.784 kJ/mol
Boiling Point: 251.463 °C at 760 mmHg
Vapour Pressure: 0.003 mmHg at 25 °C
Structure of (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol (CAS NO.156928-09-5):

Systematic Name: (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol
SMILES: O[C@H]1CO[C@H]2OCC[C@@H]12 Copy
InChI: InChI=1/C6H10O3/c7-5-3-9-6-4(5)1-2-8-6/h4-7H,1-3H2/t4-,5-,6+/m0/s1
InChIKey: RCDXYCHYMULCDZ-HCWXCVPCBF
Std. InChI: InChI=1S/C6H10O3/c7-5-3-9-6-4(5)1-2-8-6/h4-7H,1-3H2/t4-,5-,6+/m0/s1
Std. InChIKey: RCDXYCHYMULCDZ-HCWXCVPCSA-N

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

(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol (CAS NO.156928-09-5) also can be called (3R,3aS,6aR)-3-Hydroxyhexahydrofuro(2,3-b)furan ; and Furo[2,3-b]furan-3-ol, hexahydro-, (3R,3aS,6aR)- .

Product Name

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

Synthetic route

(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol Chemical Properties

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

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