Production Method 1

285-69-8

22554-74-1

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Water ;  rt → reflux; 24 h, reflux; reflux → rt
1.2 Reagents: Sodium carbonate ;  pH 8 - 9, rt

Reference

Silicate Complexes of Sugars in Aqueous Solution

Lambert, Joseph B.; Lu, Gang; Singer, Stephanie R.; Kolb, Vera M., Journal of the American Chemical Society, 2004, 126(31), 9611-9625

Production Method 2

285-69-8

22554-74-1

Reaction Conditions

1.1 Reagents: Water Catalysts: Epoxide hydrolase Solvents: Acetonitrile ,  Water ;  pH 9.0, 37 °C; 0 °C

Reference

Regio- and stereochemistry of the acid catalyzed and of a highly enantioselective enzymic hydrolysis of some epoxytetrahydrofurans

Barili, Pier Luigi; Berti, Giancarlo; Mastrorilli, Ettore, Tetrahedron, 1993, 49(28), 6263-76

Production Method 3

4358-64-9

22554-74-1

453-20-3

Reaction Conditions

1.1 Catalysts: Zirconium dioxide Solvents: 1,4-Dioxane ;  32 h, 8 atm, 453 K

Reference

Selective Hydrodeoxygenation of Cyclic Vicinal Diols to Cyclic Alcohols over Tungsten Oxide-Palladium Catalysts

Amada, Yasushi; Ota, Nobuhiko; Tamura, Masazumi; Nakagawa, Yoshinao; Tomishige, Keiichi, ChemSusChem, 2014, 7(8), 2185-2192

Production Method 4

4358-64-9

22554-74-1

453-20-3

71-36-3

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Ceria ,  Palladium ,  Rhenium oxide Solvents: 1,4-Dioxane ;  4 h, 8 MPa, 413 K

Reference

Performance, Structure, and Mechanism of ReOx-Pd/CeO2 Catalyst for Simultaneous Removal of Vicinal OH Groups with H2

Ota, Nobuhiko; Tamura, Masazumi; Nakagawa, Yoshinao; Okumura, Kazu; Tomishige, Keiichi, ACS Catalysis, 2016, 6(5), 3213-3226

Production Method 5

285-69-8

22554-74-1

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Water ;  rt → 100 °C; 6 h, 100 °C; 100 °C → rt
1.2 Reagents: Sodium carbonate Solvents: Water ;  pH 8, rt

Reference

Structure-Guided Discovery of Aminoquinazolines as Brain-Penetrant and Selective LRRK2 Inhibitors

Keylor, Mitchell H. ; Gulati, Anmol ; Kattar, Solomon D.; Johnson, Rebecca E.; Chau, Ryan W.; et al, Journal of Medicinal Chemistry, 2022, 65(1), 838-856

Production Method 6

7493-90-5

22554-74-1

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: 2427663-29-2 Solvents: 3-Octanol ;  3 h, 180 °C

Reference

N,N,O-Coordinated tricarbonylrhenium precatalysts for the aerobic deoxydehydration of diols and polyols

Li, Jing; Lutz, Martin; Klein Gebbink, Robertus J. M., Catalysis Science & Technology, 2020, 10(11), 3782-3788

Production Method 7

285-69-8

22554-74-1

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane ,  Water ;  rt → 95 °C; 24 h, 95 °C

Reference

Epoxide Hydrolase-Catalyzed Enantioselective Synthesis of Chiral 1,2-Diols via Desymmetrization of meso-Epoxides

Zhao, Lishan; Han, Bin; Huang, Zilin; Miller, Mark; Huang, Hongjun; et al, Journal of the American Chemical Society, 2004, 126(36), 11156-11157

Production Method 8

285-69-8

22554-74-1

Reaction Conditions

1.1 Reagents: Water Solvents: Water

Reference

Rearrangements of oxide rings and chemical reactions during synthesis of incomplete nitrates of α-epoxy polyhydric alcohols

Korolev, A. M.; Eremenko, L. T.; Berezina, L. I.; Lagodzinskaya, G. V.; Manelis, G. B., Izvestiya Akademii Nauk SSSR, 1975, (11), 2516-24

Production Method 9

17177-50-3

22554-74-1

1058721-16-6

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water ;  rt; 1 h, rt

Reference

Preparation of 2,3,4-Trihydroxybutylarsonic Acid: A Starting Compound for Novel Arsonolipids

Lala, Maria A.; Tsivgoulis, Gerasimos M.; Ioannou, Panayiotis V., Phosphorus, 2007, 182(12), 2747-2760

Production Method 10

7493-90-5

22554-74-1

Reaction Conditions

1.1 Catalysts: Methyltrioxorhenium Solvents: 3-Octanol ;  1.5 h, 170 °C

Reference

Deoxygenation of Biomass-Derived Feedstocks: Oxorhenium-Catalyzed Deoxydehydration of Sugars and Sugar Alcohols

Shiramizu, Mika; Toste, F. Dean, Angewandte Chemie, 2012, 51(32), 8082-8086

Production Method 11

4358-64-9

22554-74-1

453-20-3

35296-72-1

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium ,  Rhenium oxide Solvents: 1,4-Dioxane ;  4 h, 8 MPa, 413 K

Reference

Hydrodeoxygenation of Vicinal OH Groups over Heterogeneous Rhenium Catalyst Promoted by Palladium and Ceria Support

Ota, Nobuhiko; Tamura, Masazumi; Nakagawa, Yoshinao; Okumura, Kazu; Tomishige, Keiichi, Angewandte Chemie, 2015, 54(6), 1897-1900

Production Method 12

1058721-16-6

22554-74-1

2680645-60-5

Reaction Conditions

1.1 Reagents: Sodium sulfite Solvents: Water ;  6 d, rt

Reference

Preparation of (mono)sulfonates: Suitable precursors for unnatural sulfonolipids

Ioannou, Panayiotis V.; Tsivgoulis, Gerasimos M., Main Group Chemistry, 2021, 20(2), 103-118

3,4-Furandiol,tetrahydro-, (3R,4R)-rel- Raw materials

• 1,2-Ethanediol,1-(2-oxiranyl)-
• cis-Tetrahydrofuran-3,4-diol
• 1,2,3-Butanetriol, 4-chloro-
• 3,6-Dioxabicyclo[3.1.0]hexane
• DL-Threitol

3,4-Furandiol,tetrahydro-, (3R,4R)-rel- Preparation Products

• 1,2,3-Butanetriol, 4-chloro- (1058721-16-6)
• 1-Butanesulfonic acid, 2,3,4-trihydroxy-, sodium salt (1:1) (2680645-60-5)
• 3,4-Furandiol,tetrahydro-, (3R,4R)-rel- (22554-74-1)
• oxolan-3-ol (453-20-3)
• 1-Butanol (71-36-3)
• 1-Butanol (35296-72-1)

• 1. Emulsifier-free, organotellurium-mediated living radical emulsion polymerization (emulsion TERP) of styrene: poly(dimethylaminoethyl methacrylate) macro-TERP agent?
  Yukiya Kitayama Polym. Chem., 2014,5, 2784-2792
• 2. Embedding heteroatoms: an effective approach to create porphyrin-based functional materials
  Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro Osuka Dalton Trans., 2017,46, 13322-13341
• 3. Estimation of activation energy for electroporation and pore growth rate in liquid crystalline and gel phases of lipid bilayers using molecular dynamics simulations?
  Amit Kumar Majhi,Subbarao Kanchi,V. Venkataraman,K. G. Ayappa,Prabal K. Maiti Soft Matter, 2015,11, 8632-8640
• 4. Fe3O4 nanoclusters highly dispersed on a porous graphene support as an additive for improving the hydrogen storage properties of LiBH4?
  Guang Xu,Wei Zhang,Ying Zhang,Xiaoxia Zhao,Ping Wen,Di Ma RSC Adv., 2018,8, 19353-19361
• 5. Establishment and implications of a characterization method for magnetic nanoparticle using cell tracking velocimetry and magnetic susceptibility modified solutions
  Huading Zhang,Lee R. Moore,Maciej Zborowski,P. Stephen Williams,Shlomo Margel,Jeffrey J. Chalmers Analyst, 2005,130, 514-527

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Oxolanes Oxolanes
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Oxolanes

• 86087-23-2((S)-Tetrahydrofuran-3-ol)
• 4358-64-9(cis-Tetrahydrofuran-3,4-diol)
• 84976-47-6(3-Hydroxytetrahydrofuran)
• 84709-85-3((3S,4S)-Tetrahydrofuran-3,4-diol)
• 86087-24-3((3R)-oxolan-3-ol)
• 453-20-3(oxolan-3-ol)
• 104593-13-7(3-Furanol, tetrahydro-, sodium salt)
• 59727-71-8(Tetrahydrofuran-3,4-diol)
• 74217-98-4(2-Furanyl, tetrahydro-3-hydroxy-)
• 1217718-57-4((S)-(+)-3-Hydroxytetrahydrofuran-d4)