(3r,3as,6ar)-Hexahydrofuro[2,3-B]furan-3-Ol

Base Information

• Chemical Name: (3r,3as,6ar)-Hexahydrofuro[2,3-B]furan-3-Ol
• CAS No.: 156928-09-5
• Molecular Formula: C6H10O3
• Molecular Weight: 130.144
• European Community (EC) Number: 605-076-4
• DSSTox Substance ID: DTXSID80433074
• Nikkaji Number: J1.530.774I
• Wikidata: Q27465119
• Mol file: 156928-09-5.mol

Synonyms:(3R,3aS,6aR)-hexahydrofuro(2,3-b)furan-3-ol;hexahydrofuro(2,3-b)furan-3-ol

Chemical Property of (3r,3as,6ar)-Hexahydrofuro[2,3-B]furan-3-Ol

Chemical Property:

• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.51
• Boiling Point: 251.463 °C at 760 mmHg
• PKA: 14.07±0.20(Predicted)
• Flash Point: 105.881 °C
• PSA: 38.69000
• Density: 1.276 g/cm³
• LogP: -0.25990
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly, Heated)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 130.062994177
• Heavy Atom Count: 9
• Complexity: 115

Purity/Quality:

98%, ^*data from raw suppliers

(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COC2C1C(CO2)O
• Isomeric SMILES: C1CO[C@H]2[C@@H]1[C@H](CO2)O
• Uses: (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol is used as a reagent in the synthesis of Darunavir (D193500); a second generation HIV-1-protease inhibitor and antiviral agent.

Technology Process of (3r,3as,6ar)-Hexahydrofuro[2,3-B]furan-3-Ol

There total 139 articles about (3r,3as,6ar)-Hexahydrofuro[2,3-B]furan-3-Ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3-acetoxy-(3R,3αS,6αR)-bis-tetrahydrofuran (162119-35-9) → (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol (156928-09-5)

Guidance literature:

With methanol; potassium carbonate; at 20 ℃; Product distribution / selectivity;

Reference yield: 95.0%

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl benzoate (725264-69-7) → (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol (156928-09-5)

Guidance literature:

With methanol; water; sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1016/j.tetasy.2010.08.005

Reference yield: 95.0%

C6H10O4 → (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol (156928-09-5)

Guidance literature:

With hydrogenchloride; diisobutylaluminium hydride; In water; toluene; at -50 - 60 ℃; for 16h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;

upstream raw materials:

(3R,4S)-4-(2-Hydroxy-ethyl)-5-methoxy-tetrahydro-furan-3-ol

3-acetoxy-(3R,3αS,6αR)-bis-tetrahydrofuran

acetic anhydride

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

Downstream raw materials:

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-(4-nitrophenyl)carbonic acid

((1S,2S,4S)-4-Amino-1-benzyl-2-hydroxy-5-phenyl-pentyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

{(1S,3S,4S)-1-Benzyl-4-[(3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl)oxycarbonylamino]-3-hydroxy-5-phenyl-pentyl}-carbamic acid tert-butyl ester

Refernces

• 1、 Hayashi, Yumi,Aikawa, Toshiaki,Shimasaki, Yasuharu,Okamoto, Hiroaki,Tomioka, Yosuke,Miki, Takashi,Takeda, Masahiro,Ikemoto, Tetsuya. "Research and Development of an Efficient Synthesis of a Key Building Block for Anti-AIDS Drugs by Diphenylprolinol-Catalyzed Enantio- and Diastereoselective Direct Cross Aldol Reaction". . p. 1615 - 1620. Retrieved 2016.
• 2、 Kulkarni, Mukund G.,Shaikh, Yunnus B.,Borhade, Ajit S.,Dhondge, Attrimuni P.,Chavhan, Sanjay W.,Desai, Mayur P.,Birhade, Deekshaputra R.,Dhatrak, Nagorao R.,Gannimani, Ramesh. "The efficient synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol and its isomers". . p. 2394 - 2398. Retrieved 2010.
• 3、 Moore, Gary L.,Stringham, Rodger W.,Teager, David S.,Yue, Tai-Yuen. "Practical synthesis of the bicyclic darunavir side chain: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol from monopotassium isocitrate". . p. 98 - 106. Retrieved 2017.
• 4、 Black, David M.,Davis, Roman,Doan, Brian D.,Lovelace, Tom C.,Millar, Alan,Toczko, Jennifer F.,Xie, Shiping. "Highly diastereo- and enantioselective catalytic synthesis of the bis-tetrahydrofuran alcohol of Brecanavir and Darunavir". . p. 2015 - 2019. Retrieved 2008.
• 5、 -. "METHODS FOR MAKING DARUNAVIR P2-LIGAND PRECURSORS". . . Retrieved 2022/02/28.
• 6、 More, Ganesh V.,Malekar, Pushpa V.,Kalshetti, Rupali G.,Shinde, Mahesh H.,Ramana, Chepuri V.. "Ru-catalyzed asymmetric transfer hydrogenation of α-acyl butyrolactone via dynamic kinetic resolution: Asymmetric synthesis of bis-THF alcohol intermediate of darunavir". . . Retrieved 2021/02/16.