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

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

 EINECS 605-076-4
CAS No. 156928-09-5 Density 1.276 g/cm3
PSA 38.69000 LogP -0.25990
Solubility N/A Melting Point N/A
Formula C6H10O3 Boiling Point 251.463 °C at 760 mmHg
Molecular Weight 130.144 Flash Point 105.881 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 156928-09-5 ((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol) Hazard Symbols N/A
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;

Article Data 50

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

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
ConditionsYield
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
ConditionsYield
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

(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)- .

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